


Old Flames

by thelonelywriter



Category: Supernatural
Genre: Anal Fingering, Anal Sex, Banter, Blow Jobs, Bottom Castiel, Cuddling & Snuggling, Dirty Talk, Double Penetration, Fluff, Fluff and Smut, Hand Jobs, Kink Negotiation, Light Spanking, Lots of kissing, M/M, Panty Kink, Polyamory, Polyamory Negotiations, Power Bottom Castiel, Rimming, Sassy Castiel, Size Kink, Smut, Threesome, Threesome - M/M/M, Top Benny, Top Dean, Twink Castiel, Weird Plot Shit, how did i even write this, like if you squint - Freeform, smooch smooch, somewhat of a dean smith 'verse
Language: English
Status: Completed
Published: 2017-03-10
Updated: 2017-03-10
Packaged: 2018-10-02 04:48:25
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 25,042
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/10209947
Author URL: https://archiveofourown.org/users/thelonelywriter/pseuds/thelonelywriter
Summary: “Dean, you and Cas,” Benny began, tilting his head, looking down at his beer that was nearly gone. “You and Cas have been together for awhile,” Benny stated.“Yeah, a few years,” Dean offered.“You two seem very happy together,” Benny said, glancing over at Dean. Dean nodded, smiled softly.“We are,” Dean said. And then, he took a step forwards, a step that was probably dangerous, at least slightly. “And we’re very open at this point, with each other, y’know, with what we want,” Dean told Benny, giving him a suggestive look. Understanding seemed to flicker in Benny’s eyes.“There a reason you’ve been comin’ to see me so often?” Benny asked calmly, his voice just a little lower, spoken in a tone that made Dean shiver. Dean swallowed thickly, looked over at Benny. They made eye contact for what felt like months to Dean but was actually a few seconds.~or~The one where Cas and Dean find Benny, an old lover of Dean's, and Cas gets all too good of an idea.





	

**Author's Note:**

> so there was once a time in my life wherein i said to myself 'the one thing you will /never/ write is double penetration' then,,,, gabe happened. my absolutely wonderful, beautiful, kinky friend gabe gave me the idea to write a dp threesome w/ dean and cas and benny and i went to do that but then i had to fix some things and add some things and i honest to god thought maybe 10k words at max but uh it's a lot longer????? i have never written dp nor have i dabbled in polyamory so if any of ya'll know anything about any of that, feel free to fuckin' school me, i don't know what i'm doing rarely do i ever okay

“Dean, I know you like to hear the whole, ‘Okay, you’re right,’ spiel, but I apologize in advance. I can’t give it to you. We’re lost,” Cas announced firmly and matter of factly from his place in the passenger seat of Dean’s car. Dean huffed a breath, glancing out his window, away from the straight, long road in front of them that was bordered by fields. On their way home from a long day at work, Dean insisted on the scenic route. Cas had rolled his eyes but figured, what harm could it do? Turns out it could do enough because they were lost now in some rural farm town.

Cas was highly unamused. Or, possibly, slightly amused because it was always interesting to see how Dean dealt with things like this. Usually, not well, however.

“We’re not _lost_ , Cas,” Dean argued.

“We’re lost,” Cas shot back readily. Dean huffed another breath and pursed his lips, pointedly not looking Cas’ way. “And I have no cell reception, and what kind of idiot doesn’t keep a map in his car?”

“Hey!” Dean said indignantly, finally looking over at Cas who definitely looked highly unamused. Dean sighed defeatedly, looked back ahead of him, at all the Goddamned fields. Dean heard Cas sigh next to him, then glanced over to see him slump down a little in the seat, prop his now bare feet up on the dashboard. Dean gave him a warning look but Cas just shrugged. Dean debated telling him to put his feet back down but he knew Cas would probably defy orders anyway.

“Okay,” Cas began, awkwardly attempting at shrugging off his suit jacket. Cas honestly hated wearing suits, but working as Dean’s assistant at Sandover, he had to wear one everyday. Which, he loathed, but Dean always seemed to like the look of Cas in a suit.

“If you can find a food place, I’ll hold back my wrath on you,” Cas told Dean. Dean raised an eyebrow, but didn’t look Cas’ way.

“Oh, your wrath?” Dean supposed.

“Yeah,” Cas grunted as he got one arm out of the sleeve of his jacket. Dean sighed again because, alright, Cas could get a little wrathful when he was really really hungry. “I’m starting to get hungry,” Cas went on as he continued to struggle with his jacket.

“We’re not in some movie, Cas, this isn’t the scenario where the couple is lost and driving through friggin’,” Dean flailed a hand. “Wheat fields!” he exclaimed, glancing over at one field with tall tall grass that probably wasn’t wheat but hey, Dean improvises. “And then the couple finds like a diner or whatever. Or a gas station,” Dean went on.

“What if it’s like that movie ‘ _Jeepers Creepers_ ’?” Cas questioned, finally getting his jacket off and throwing it into the backseat. Dean looked over at him and raised an eyebrow. “Remember, those people, brother and sister, driving the scenic way home. The crazed thing, I forget the name, something horror movie-ish, comes out of nowhere in that car. Follows them around. Dumps the bodies in that chute to the church and-”

“What are you talking about?” Dean inquired, shaking his head and glancing over at Cas.

“That movie, we watched it together like, a few months ago or something. That was the plot,” Cas told Dean rather nonchalantly. Dean just shook his head.

“Yeah, alright.”

“What I’m saying is, we’re probably gonna die out here, Dean,” Cas sighed. Dean could tell that Cas was joking, trying to lighten the mood a little, which, he appreciated. A joking Cas was a hell of a lot better than a pissy Cas.

“We’re not gonna _die_ , Cas,” Dean assured Cas.

“Dean, you even said it yourself, it’s not like we’re gonna find some gas station, or hotel, or diner, or any possible sign of-”

“Ha!” Dean exclaimed out of nowhere.

“What?” Cas asked, looking around.

“Diner, right up there. See it? The sign’s already lit up,” Dean pointed out, pointing to his side of the road where, sure enough, on the horizon where the sun was receding, there was what looked like a little diner, probably worn out. Cas poked his head up, straightened up and dropped his feet down to the floor of the car. 

“Don’t say-”

“I was right,” Dean interrupted. Cas closed his eyes and nodded.

“You said it,” he pointed out inanely. When he opened his eyes and looked over at Dean, Dean had that stupid, smug smile on that made Cas’ stomach flip, even though, he was still just slightly pissed at Dean for getting them lost in the first place. But, it didn’t really matter as they pulled into the dusty parking lot with only a few other cars in it, because Cas was getting _food_ , and food was very very important.

“We’re still lost,” Cas told Dean as he slipped his shoes back on and got out of the car.

“We’ll get directions in here,” Dean said, stepping out of the car too.

Cas groaned and stretched a little, looked over the diner. It looked worn down, kind of a classic that fit pretty well with the land. Nonetheless it was nice, and Cas went on to look through the windows, the door. It looked slightly old fashioned, and Cas was admiring that just a bit when something caught his eye. Someone. 

Inside the diner was some guy who was fucking built. He was working behind the counter, judging by his rolled up sleeves and the apron wrapped around him, Cas would have taken a guess that he was the cook. Cas couldn’t see the details of him, but he could tell that whoever that guy was he was hot, he was built, and he was-

“Holy shit,” Dean murmured almost wonderingly as he stepped next to Cas. Cas glanced over at him and saw that his gaze was directed at the same guy Cas had been looking at.

“Yeah, no kidding,” Cas joined in. “He’s so built,” Cas mused. “Jesus,” Cas said quietly, watching him move behind the counter, turn his back so that it was facing Cas. “I would definitely let him- Ow!”

Cas was cut off when Dean gave a sharp smack to his arm. Cas brought his hand up to his arm and rubbed over it a little. 

“What? I’m just saying-”

“No, no, I know, it’s just, I know him,” Dean told Cas. Cas’ eyebrows nearly went to his hairline.

“You know that guy?” he questioned incredulously.

“That’s, that’s Benny, I knew him in college. We were… actually we were roommates,” Dean went on, his voice slightly soft. Cas gaped at him.

“You’re shitting me,” Cas said simply after a short silence because there was absolutely no way that Dean could find his college roommate working at some diner in the middle of nowhere. But…

“No, I’m not. Benny Lafitte. We roomed together for a few years,” Dean told Cas. Cas blinked and blinked before sighing and shaking his head.

“Yeah, okay, we’re definitely in some freaky ass movie where- Dean, what-?” Cas began as Dean’s hand came out and grabbed Cas’ arm as Cas began to walk towards the door.

“Maybe we should find another diner,” Dean suggested, trying to pull Cas back towards him. Cas shot Dean an incredulous look and pulled his arm away from Dean’s grasp.

“You’re serious?”

Dean gave Cas a look that portrayed that he was ever so serious. 

“No.” Cas shook his head. “First of all, I don’t think we could find another diner in a fifty mile radius, second of all, I’m hungry,” Cas went on, taking more steps towards the door of the diner. “And you get to meet up with an old friend,” Cas offered as Dean followed him hesitantly.

“Cas, you don’t under-”

But, before Dean could get the word ‘understand’ out of his mouth, Cas was opening the door to the diner, bells above it chiming as he stepped over the threshold, Dean following with an impending sense of doom.

Cas let out a breath of air, looked around and took in the sight of the diner. It was obvious that it was nice and clean, a lot more telling that the outside. That and the wonderful smell of food. Cas smiled a little before glancing over at who was supposedly “Benny” who was one of the only ones behind the counter. There was one or two women, but Benny was the one that caught Cas’ attention.

Benny turned, having heard the chiming of the bells and looked over at Cas. Cas immediately saw kind eyes, a warm little smile spreading over Benny’s face. 

“Hey there.”

Oh, God, he had an accent. Cas was a sucker for accents. Cas swallowed, decided to put on that innocent, virginal act that he mastered very well being as young as he was. He wasn’t fresh out of college, but almost. He was over a few years younger than Dean, something that he knew caught Dean’s eye the second they had met. Cas had a thing for older guys, Dean had a thing for younger guys. Cas also had a thing for built guys with thick, southern accents. And though he knew he wasn’t taking Benny home, though he knew that he was and always would be faithful to Dean, he figured he could at least tease. Besides, he knew Dean got off on the possessive art of things, of knowing that no matter how much Cas flirted with other guys, Dean would always be the only one to have him.

“Hi,” Cas replied sweetly, taking a step aside to let Dean stand next to him. Though, for some reason, Dean seemed unusually shy.

“Well, you two look like you came from out of town,” Benny supposed, swiping a rag over the linoleum counter.

“Well, we sort of got a little lost,” Cas told Benny, giving him a coy smile before turning to Dean. He looked up at Dean who gave him a sort of wide eyed look. Cas just raised an eyebrow before Dean turned to face Benny too. Cas turned back to look at Benny, and he watched a look of recognition, combined with interest, dawn on his face.

“Wait a second,” he began, leaning forwards a bit, eyeing Dean. “Winchester?”

Dean swallowed thickly. God, he hadn’t heard that voice in a long time.

“Still remember me?” Dean asked, trying to keep things light, trying not to let his voice betray him and crack.

“Well, ‘course I do. We roomed, what, three years?” Benny questioned, grinning at this point.

“Three years,” Dean repeated with a nod.

“Hey, it’s great to see you again. Knew when we parted I wouldn’t be seeing the last of you,” Benny teased, gaining a little laugh from Dean. “And who’s this?” Benny questioned, his gaze turning on Cas who nearly beamed with satisfaction. Cas had to admit that one of his favorite things was letting people know that he was with Dean. 

“This is Castiel,” Dean sighed, looking fondly over at Cas with a little smile.

“You can call me Cas,” Cas chirped, gaining a nod from Benny.

“Well, it’s very nice to meet you, Cas,” Benny told him, leaning his forearms on the counter. “I’m Benny, just in case Dean hasn’t told you already,” Benny told Cas.

“It’s nice to meet you, Benny,” Cas replied happily.

“Why don’t you two sit down? You look a little hungry,” Benny noted, straightening back up again. Cas nodded, stepping forwards with Dean following. 

The counter was set up with high stools bolted into the floor, and Cas slid into one with ease, watching Dean do the same.

“Well, I said I knew I hadn’t see the last of you, but I never suspected seeing you wandering in here from the fact you got lost,” Benny said, looking amused. Dean huffed a breath of laughter and shook his head.

“Yeah, admittedly, I took a wrong turn, started driving down this rural road,” Dean told Benny. 

“Well, I gotta admit, I’m a little glad you did. I haven’t seen you in ages,” Benny drawled, pulling out two menus and placing them in front of Dean and Cas. “What’ve you been up to?” Benny questioned, tossing the rag aside.

“Sales, marketing at Sandover,” Dean sighed. Benny nodded, raised an eyebrow.

“That sure is impressive. Big company, isn’t it?” Benny questioned. Dean nodded. “That must be some hard work,” Benny went on. Dean laughed a little, nodding.

“Well, Cas makes it easier, I have to admit,” Dean said, nudging Cas who couldn’t help but grin and look down in his lap. “He’s my PA, helps with a lot of the paperwork, a lot of the small stuff that counts as big stuff to me,” Dean said.

“You’re lucky,” Benny huffed. “I could use my own PA around here,” he went on.

“You own this place?” Dean said, though he said it more as a statement than a question since the answer seemed rather obvious. Sure enough, Benny nodded.

“I’ve been here for awhile, just saving up for something bigger. Doesn’t make a lot of money but I wanted to do something culinary. This place isn’t so bad, though, gotta admit. Not too many folks stop by, but when they do some come back which I would say counts as something,” Benny told Dean and Cas.

“I would say so,” Dean agreed, nodding his head. There was a short pause before Benny spoke up again.

“Well, I’ve gotta get some food for you two. Anything on the menu,” he offered kindly, an offer than just had to be taken up.

\---

It was hours later and one of the best burgers Cas had ever had later when Dean and Cas were heading back home, thankfully, with directions given to them by Benny.

“We’ll have to go back sometime,” Cas proposed as he glanced out the window, watched the now dark fields pass by. Dean made some noise of indifference, and Cas thought for a moment. 

Dean and Benny had seemed pretty close during their encounter. During most of their meal Benny was talking with them, catching up with Dean, asking Cas some questions about his own schooling, his career. But, Cas still had that lurking remembrance of how Dean had been reluctant, shy almost, when they initially went in, and even during some of the conversation. The conversation was never awkward or anything, but Cas got a strange feeling from Dean at certain points. And then with the way Benny talked, with some of the looks they had shared… Cas was a little curious.

“So, you and Benny were good friends?” Cas questioned, starting to lead up to something, build something up. Dean shrugged though.

“I mean, yeah. He was, _is_ , really nice,” Dean told Cas. Cas nodded. They had discussed college a bit, Dean had been majoring in something different than Benny, but they still got paired to a room in sophomore year, then kept that set up through the rest of the years.

“You guys seem close,” Cas supposed. Dean shifted in his seat.

“Well, yeah. We were good friends. Pretty much best friends,” Dean added on, sounding almost reverent.

“Best friends,” Cas repeated.

“Yeah,” Dean agreed simply. He paused before glancing over at Cas. “Why?” Dean questioned.

“No, it’s just, the way you two interact it shows,” cas said calmly.

“Shows what?” Dean immediately said. Cas had to hide a smile. He could tell Dean was getting uncomfortable and it was only solidifying his suspicion.

“Nothing,” Cas sighed, looking back out the window and trying to brush it off because he knew that would only make Dean more worked up.

“What?” Dean repeated.

“Nothing.”

“Cas,” Dean said, his tone warning. Cas bit his lip.

“Just friends?” Cas questioned. Dean hesitated, then sighed.

“Cas, it’s not, we weren’t,” Dean began, though Cas cut him off.

“Dean, it’s fine.”

Dean glanced over at Cas, into eyes darkened by the night. He didn’t look for long, he had to keep his eyes on the road, but when he did look he caught kindness. And a kind of welcoming, a sort of comfort Dean knew he could fall back into. Dean sighed defeatedly and looked back at the road.

“We were… a thing. Kind of. Sort of dating-ish. We just kind of cut it off, we weren’t like, majorly in love with each other or anything, it was never anything like it is with you right now,” Dean explained. Cas simply nodded.

“He’s hot,” Cas said simply. Dean stuttered.

“Uh,” Dean said stupidly because he wasn’t sure what Cas’ aim was on this. Cas seemed to know that though.

“And no, I’m not like, trying to get you to agree so I can go off at you. I’m just saying, he’s hot. I’d let him fuck me.”

Dean choked and Cas grinned. Then it dawned on him.

“Wait a second,” Cas said, tone suddenly urgent. “Did you… did you bottom when you were with him?” Cas questioned, shifting in his seat, looking over at Dean. 

“Cas,” Dean said, as though he were asking him to shut up. Cas just smiled. He could tell, even through the dark, that Dean was blushing.

“Holy shit, you totally did,” Cas said, sounding a little amused. Or a lot. “I mean, I know we’ve switched a few times and you’ve bottomed, but you’ve never seemed to really like it as much as I do,” Cas mused, which was true. They had switched here and there just to experiment, but in general Cas usually bottomed and tended to be more submissive. And, usually, Cas had a hard time imagining Dean as a sub or a bottom, but seeing Benny next to him… 

“You were a total sub,” Cas stated.

“Cas,” Dean said simply, not daring deny it since, alright, maybe it was true.

“Jesus, if he could turn you into a sub…” Cas began, trailing off. Dean glanced over at him.

“What?” Dean questioned cautiously.

“Oh, nothing,” Cas sighed. “Just wondering how he’d handle me.”

“What, if he was fucking you?” Dean questioned straightforwardly. Sure, him and Cas were pretty monogamous, but they had figured they didn’t really have a problem mentioning a third party off hand, or imagining a third party joining them. They just hadn’t really thought about actually adding a third party though.

“I mean, yeah,” Cas replied with a shrug. Cas turned to Dean, grinning. “Was he a good fuck?”

Dean glanced back over at Cas with a raised eyebrow.

“You really wanna know?” Dean questioned. Cas gave him a look that said it all. Dean let out a sigh. “Yeah, he was,” Dean told Cas.

“I bet he’s hung.”

“You have no shame,” Dean informed Cas, shaking his head. Cas just laughed all sweetly at that.

“Dean, you can’t blame me, he’s fucking hot, and he’s built, that scruff, those arms, I mean God,” Cas sighed.

“What, so you’d prefer him over me?” Dean questioned. Cas’ grin grew impish.

“Well, obviously I’d prefer you, but I mean, it’d be nice to have both of you,” Cas told Dean, glancing over at him. 

“A threesome with Benny?” Dean said, phrasing it as somewhat of a question.

“It’d be perfect!” Cas argued. “All that tension you two have from years apart, the fact that I’d love to take his cock, the fact that I love you overall,” Cas added on.

“Okay, how do you know he wants it?” Dean questioned, and he felt like somewhat of an idiot for even going along on this hypothetical train of questions with Cas.

“I saw the way he looked at you,” Cas told Dean knowingly. “And, I don’t think he’d necessarily mind getting a piece of me next to you.”

Dean snorted at that, and Cas gave his arm a light slap.

“Yeah, okay, I don’t think he’d mind getting a piece of you. Jesus, Cas, with the way you flirt like some innocent virgin I think you could get a wide array of people to go after you,” Dean mused.

“Well, I don’t need people going after me. I have you,” Cas said sweetly. Dean raised an eyebrow.

“Why these questions about Benny then?” Dean asked. Cas shrugged.

“Because Benny caught my eye and not only I, but you also like him. You’re interested too. I mean, if he fucked you good, imagine him fucking me. Imagine getting to watch,” Cas said with a devilish smile. Dean let out a groan at the imagery that was brought to mind by Cas’ words. It was good enough when Dean got to watch Cas finger himself or fuck himself on a dildo, but a real life person… 

“It’s hot, isn’t it?” Cas questioned.

“Yeah, alright,” Dean relented.

“But there’s so much more we could do,” Cas pointed out. “Do you think I could take both of you?” Cas inquired.

“Christ, Cas,” Dean managed. 

“How big is he?” Cas questioned. Dean let out a long breath and shook his head.

“I mean, I haven’t seen him since college but,” Dean sighed. “He was pretty big. Like, one of the biggest guys I’ve seen,” Dean told Cas.

“Shit,” Cas said with wonder in his tone. Dean was big enough himself, so Cas could only image Benny…

“Cas, it’s not like any of this is gonna happen,” Dean told Cas, glancing his way. 

“Yeah, but can’t you imagine? I could ride you and he could get me from behind. Or I could suck you off, he could fuck me, and then you could watch,” Cas proposed, his cock twitching in his slacks.

“Cas, I’m gonna drive off the road if you keep talking like this,” Dean warned.

“Dean, it’d be so fucking hot,” Cas said almost pleadingly. “I mean, would you want it? Would you be okay with it?” he went on. 

“I mean, yeah,” Dean sighed after a short pause. “I’d like it, but it’d Benny who it all depends on. I have no idea how Benny would feel about it, I haven’t talked to him in years. Do you think I could just walk back in there and say, ‘Oh, hey, Benny, I was wondering if you wanted to have a threesome with my boyfriend of two years’,” Dean said. Cas just gave him a look resembling the look of a sad puppy, and Dean scoffed.

“It could work, Dean, it could, I swear,” Cas insisted.

“You’re delusional,” Dean said, but Cas shook his head.

“Dean, can’t you imagine it though? All the things we could do? I could get both of you to come on my face at the same time. Benny could fuck you and I could suck you off. You could even just sit back and watch Benny fuck me. You wouldn’t even have to do anything, you could just get yourself off,” Cas supposed, his voice unnaturally hopeful. Dean groaned again, his knuckles white on the steering wheel.

“Fuck, Cas.”

“It’s hot, isn’t it?” 

“Yeah, it’s hot, but it can’t happen,” Dean argued.

“But why?” Cas asked, his voice verging on a whine. Dean opened his mouth, then closed it. Cas was making an unusually suggestive and valid case that Dean was finding hard to argue with the more they talked.

“You’d be okay with bringing in a third party? You know this would change the relationship dynamic,” Dean supposed, glancing over at Cas.

“I know,” Cas replied. “As long as we talked it over, as long as you were okay with it and you were consenting and willing, I would do it,” Cas told Dean. Dean stole one last glance at Cas before looking back at the road, letting a silence settle between them, nothing tense or unhappy, just something filled with what was seemingly thought.

Dean thought over him and Benny a bit. It didn’t seem to bother Cas, which Dean was thankful for. The only thing it did do that was negative was make Dean a little on edge. Not in a necessarily bad way, just in a way that Dean was a little insecure, didn’t know how Benny was feeling. Benny seemed fairly at ease, however, the whole time they were talking. His eyes still had that warmth, that light that had pulled Dean in when he first met him. 

Dean found, thinking over it, that he wouldn’t mind exploring things further, he just wasn’t sure how to go about things. He wasn’t an expert in threesomes, nor polyamory, he didn’t really know what step one was. And he was pretty sure Wikihow didn’t have a page for that. 

“You honestly think we can make this work?” Dean sighed. Cas nodded.

“With thought, and consent, and planning, yes, I think we can.”

“Alright. If you say so.”

\---

The next morning, luckily a Saturday, Dean woke up with Cas curled around him, nuzzling his head into Dean’s chest. Dean stretched and Cas stirred, clinging onto Dean a little tighter, something that Dean had to smile at. Dean ran a hand up Cas’ back, fingers curling around the back of his neck, finding the hairs that curled at the nape of it and toying with them.

Dean stayed like that for a moment, figuring Cas was still asleep before Cas finally stretched a little. 

“Are you awake?” Cas mumbled into Dean’s chest. Dean leaned down, pressed a kiss to the crown of Cas’ head where some impressive be head was going on. 

“Mhm,” Dean hummed in reply. Cas groaned and stretched, then yawned before only tightening his grip around Dean. 

“‘Morning,” Cas murmured sleepily. 

“‘Morning, sweetheart,” Dean replied. 

“What’s for breakfast?” Cas questioned, voice still sleep ridden, slightly rough. 

“I’ll make pancakes if you want,” Dean offered. Cas hummed happily and nodded. 

“Yes. Please do,” he replied. Dean smiled, kissed Cas’ head once more, let his hand wander up to card through his hair. 

A silence fell between them, sleepy and soft, nothing urgent, nothing uncomfortable. Dean took in the heat of Cas’ body against him, the feel of his breath, his heartbeat. Dean took a second to think over the night before, over what he had been thinking about before him and Cas had crawled into bed. And then he remembered. Dean cleared his throat, shifted around a bit. 

“Cas?”

“Hm?”

“You remember last night, what we talked about and everything, right?” Dean questioned. Cas snorted. 

“I’m not gonna forget that anytime soon, Dean,” Cas told Dean who couldn’t help but smile. 

“Yeah, alright, just wanted to make sure,” Dean sighed. 

“Why?” Cas questioned. “Did you want to take it back? Retreat the offer?”

“No, no,” Dean shook his head. “I just think we should talk some more about it, figure out what we’re gonna do,” Dean told Cas. 

“I’ll get my dry erase board, markers, take down some notes,” Cas joked. Dean nudged him with his leg and Cas chuckled. 

“We just need to discuss it before we do anything,” Dean told Cas softly. Cas took a deep breath, suppressed a yawn. 

“I say you start with Benny. Just you and Benny. Start talking to him again and see what he’s been up to. Obviously don’t go up and ask him to join in on a threesome, but do some subtle flirting, some hints here and there,” Cas said. Dean paused. 

“You wouldn’t mind me, like, flirting with him?” Dean questioned. 

“I mean, not particularly. I know that you and I are, y’know, together, I don’t think that we should just go flirting with random people. But this is different. We both want him, collectively, right?” Cas pointed out, poking his head up and looking at Dean. “If you’re uncomfortable with it, though, we can talk about something else, take another approach,” Cas offered. 

“No, I mean, as long as you’re okay with it. It’s just gonna feel weird. You know I love you, right? Like a lot?”

Cas grinned widely and nodded. 

“I was under the impression.”

Dean nudged Cas again and Cas laughed, soft and sweet, something nice to break the haze of morning. 

“Listen, I’m not gonna do anything behind your back, okay? And I think we definitely need to talk to Benny at one point or another,” Dean supposed. 

“After you get comfortable with him, yeah. Then I can come into the picture and we can all discuss it,” Cas suggested. 

“And I’m not going past flirting with him, as a rule. For now, at least,” Dean added on. 

“I’m fine with that,” Cas nodded. “And if you do slip up, I won’t be mad,” Cas assured Dean. Dean took a deep breath and nodded. 

“What do we do afterwards? If we just… have a threesome. Then what? Does he like… come live with us?” Dean asked hesitantly. Cas hummed. 

“I don’t know about that,” Cas said. “I don’t know if I could handle having both of you around like, twenty four seven. Plus, he probably has his own place,” Cas shrugged. 

“So what, we just ask him for sex?” Dean questioned. Cas let out a breath. 

“I think we should leave the line open. Not just have a threesome and kick him out. Just, let him do his thing and if he wants us, see how we feel. If we want him, see how he feels,” Cas proposed. Dean bit his lip. 

“This could get messy,” Dean said. Cas sighed. 

“I guess you’re right. But do you want it enough to have that possibility?” Cas questioned, looking back up at Dean. Dean looked down at Cas. His eyes were thoughtful, almost hopeful. 

“Do you?” Dean asked softly. 

“As long as you’re willing,” Cas replied, keeping eye contact with Dean. Dean sighed. 

“I think so.”

\---

It was the next day, Sunday, that Cas and Dean collectively figured that Dean could head back to Benny’s diner to talk, catch up a little. Cas and Dean figured it would be best if Cas just stayed behind, that way it would probably lead to a looser, more personal conversation with Benny. Which, thankfully, it did.

When Dean had come back, Benny seemed pleasantly surprised, sat Dean down and leaned over the counter to talk to him. The conversation seemed to flow easily on both their sides. Dean was a little nervous at first, admittedly, but Benny seemed to be pretty much the same as he was in the way Dean remembered him, warm and happy and welcoming.

It was strange, Dean thought, as he watched Benny talk, to recall all the things they had done together. They had a good relationship, but they never seemed to click in the romantic sort of way that Dean and Cas had when they had met. Dean and Benny definitely had the sexual side of things under their belts, but the ‘I love you’s’, the hand holding and romantic kisses, they never seemed to master. Neither of them seemed to mind much, however. Their relationship was satisfying, and not just sexually, but emotionally. They were friends, really good friends, and that contributed to a lot of their relationship and the dynamic.

“So, you and Cas now?” Benny questioned with a twinkle in his eye as they changed the subject from what friends they had kept or lost since college. Dean immediately felt his heart jump as he nodded. “How’d you two meet?” Benny asked, tilting his head just slightly. Dean took in a breath and let it out.

“Well, he was interning after college at Sandover and had to start off low in the ranks. Just had to start off somewhere simple. He didn’t really have any other options that the ones my boss gave him, so, somehow, he ended up with me, just a PA. Initially, I felt kinda bad for him just because I could tell he was so smart, should have probably been the head of Accounting or something,” Dean huffed. “But, he just shook his head and told me he didn’t want to move up in the ranks like that, didn’t want to stay in the Business industry. Like he told you the other day, he’s more into Environmental Studies, but wanted to get some background in Business before he set off on that,” Dean explained.

“But he’s sticking with you at Sandover still?” Benny asked, looking slightly amused. Dean smiled a little sheepishly.

“Yeah, it’s kind of a thing on the side. He’s working towards finding the right job, he’s dabbled in a few other ones off to the side, but he likes working with me and I like working with him,” Dean told Benny.

“You guys must see a lot of one another then. You live together, right?” Benny inquired. Dean nodded.

“Yeah, we do, but he tells me when he’s sick of me,” Dean joked, and Benny laughed, a sound that Dean found he might have missed, just a little. “So, you’re not… with anyone?” Dean began, cautious and careful, not wanting to be too straightforward, but feeling relaxed enough in the conversation to ask. Benny, to Dean’s relief, shook his head.

“Just me here,” Benny said, looking around at the near empty diner. 

“You must get lonely,” Dean supposed, still treading carefully. Benny glanced over at Dean, just quickly, and if Dean wasn’t mistaken, there was a flash of something in Benny’s eye. Something Dean didn’t really know how to identify.

“Well, not as much as one would think,” Benny sighed. “The diner is a nice distraction, and I only live a few miles away from here, down in town. It’s a small town and everything, off the map, but everyone there is real nice, real welcoming.”

“You said you’ve been here for over a few years?” Dean questioned, picking up his drink. Benny nodded.

“After majoring in Culinary Arts in college, obviously I wanted to work in that field. There weren’t many places hiring though so I started looking at places off the map. Found this diner for sale and figured I could fix it up a little and then get a place in the town over,” Benny went on to tell Dean.

“Well, it’s a nice setup,” Dean agreed, looking around a little.

“Yeah,” Benny sighed. “But, you do have a point there, it does get lonely here and there. Not too many people stay at the diner. Guess it’s just fate that you happened to show up,” Benny said with a grin. Dean swallowed and smiled.

“Yeah, yeah, I guess it is fate,” Dean agreed.

“But you got quite a different life,” Benny sighed. 

“Well, that doesn’t mean I can’t come down here every now and then,” Dean argued. Benny smiled a little.

“Suppose you’re right.”

“We should go out for a drink or something sometimes,” Dean said carefully, glancing up at Benny. Benny had a curious look in his eye, but he smiled a little and nodded.

“Yeah. Do some catching up.”

“Catching up,” Dean repeated, nodding.

“It seems like it’s been a lifetime since college,” Benny sighed, shaking his head. Dean swallowed again but nodded. 

“It does, doesn’t it?”

\---

Dean went home that night feeling a little more comfortable, more relaxed. Him and Benny had talked for awhile, all about different things. They never talked about their relationship though, and it didn’t seem to be a huge, lurking thing. It seemed as though it was off to the side for both of them. They didn’t seem to be thinking about it that much. Instead, they talked about what happened after college, what they did and had done, people they had forgotten about over time, people they had met. It was nice, it was very nice.

Dean came home and opened the door to find Cas splayed out on the couch with a pack of twizzlers on his stomach, looking particularly comfortable and watching something on TV, the lights in the living room dim. Cas immediately perked up a little when Dean came in the door, hanging up his coat.

“There you are. Thought you might never return. Or, you’d get lost on that road again,” Cas teased, not bothering moving on the couch, just looking over at Dean with a sly grin.

“Ha ha, very funny, Cas,” Dean said blandly, kicking off his shoes, walking over to Cas who just chuckled as little. 

“No, but how’d it go?” Cas questioned as Dean leaned over to press a kiss to Cas’ lips.

“Good,” Dean hummed. Dean went to sit on the other end of the couch where Cas’ legs were, but Cas stopped him, reaching out an arm and flailing a twizzler in Dean’s direction. Dean smiled, taking the twizzler from Cas who smiled back.

“You guys talked a lot?” Cas inquired as Dean took the twizzler between his teeth, then reached down and pushed Cas’ legs off the couch so he could sit too. Cas immediately propped his legs back up on Dean’s lap when Dean had sat down.

“Yeah,” Dean replied, taking a bite of the twizzler.

“About what?” Cas questioned. Dean shrugged.

“Basic stuff. Days after college, people we knew, people we lost contact with. We never really talked about anything too deep. I learned he isn’t with anyone though, he lives in the town near his diner. Says he gets a little lonely now and then,” Dean told Cas, glancing over at him. Cas nodded.

“Sounds promising,” Cas supposed.

“I told him we should go out for drinks, we kind of planned on going this Friday. As long as that’s okay with you,” Dean added on quickly. Cas waved a dismissive hand.

“It’s fine. Even if this thing doesn’t work out, it’s good for you to have a friend, like a good college friend,” Cas pointed out. Dean hummed, nodded.

“Suppose you’re right,” Dean sighed.

“Did he say anything about me?” Cas questioned, idly twirling a twizzler in hand.

“He asked about you, asked how we met. I told him how you harassed me until I asked you out,” Dean joked. That earned a twizzler being flung his way, smacking him in the arm and falling down to the couch. Dean glanced over at Cas who was smiling, biting his lip. Dean just shrugged. “Joke’s on you, now I have a twizzler,” Dean stated, picking up the twizzler.

“I didn’t harass you. I flirted with you,” Cas shrugged.

“Okay, that’s debatable,” Dean argued. Cas nudged Dean with his foot.

“Oh shut up. You were hot. _Are_ hot,” Cas corrected. “I just had to be more… promiscuous than usual,” Cas said nonchalantly. 

“Well,” Dean sighed, patting Cas’ leg. “Guess it worked,” he said, looking over at Cas who grinned.

“Glad it did,” Cas told Dean.

“Yeah, me too,” Dean replied, smiling back over at Cas before letting his head loll back on the couch.

“Hey, you told me you and Benny broke it off but you never really told me how it happened,” Cas said after a pause, his voice curious. Dean shrugged, took a breath and let it out.

“Well, we dated for awhile but when it came to graduation, senior year, we kind of talked things over. Benny and I never had a really romantic connection, not like I have with you. We were always more of good good friends if you counted out the sex,” Dean explained. Cas raised an eyebrow.

“So was it like ‘no strings attached’?” Cas questioned. 

“No, not exactly,” Dean shook his head. “I mean, people knew about us, it was just that’s how our dynamic was. It wasn’t like we never cuddled or kissed, but it was just a different sort of relationship than ours,” Dean said, gesturing between him and Cas. “And looking back, it seems like the relationship we have is a lot more ideal.”

“Well, that’s refreshing to hear,” Cas said with a little grin.

“We just decided that with our different majors, different goals, how the relationship was playing out, we weren’t connected enough to continue on and sacrifice really important, big things for each other, y’know? It’s not like it didn’t hurt though, it took me awhile to get over him,” Dean sighed. “But, it seemed to be for the better and we both sort of agreed on that,” Dean added on, looking back over at Cas.

“Huh,” Cas said simply, looking as if he were processing things, thinking them over, taking in Dean’s words. 

“Yeah,” Dean sighed back in reply. “I have to admit I’m interested in how he reacts to this,” Dean mused.

“Well, you know him more than I do,” Cas supposed. Dean nodded.

“You’re right.”

“So, what’s your guess then?” Cas questioned. Dean glanced over at Cas who had a raised eyebrow and a twizzler between his lips. Dean eyed him for a second, thought of what it would be like to share Cas with someone else. But, Benny wasn’t exactly ‘someone else’, and Dean wasn’t on bad terms with him.

“Honestly, I’m not so sure. But, I hope it’s good.”

\---

It took a lot less longer than Dean thought for Benny to catch on. Dean and Benny had taken to going out for drinks about every Friday for a few weeks. They talked and caught up a lot, and subtle flirtations were put here and there by Dean, flirtations that Benny seemed to respect. He never seemed to ask about them or go along with them, he seemed to take them into consideration almost. Dean wasn’t really sure what the next step was, he just kept up that act until finally, out at a nearly empty bar on a Friday, Benny spoke up, threw Dean a bone that Dean eagerly took.

“Dean, you and Cas,” Benny began, tilting his head, looking down at his beer that was nearly gone. “You and Cas have been together for awhile,” Benny stated. 

“Yeah, a few years,” Dean offered.

“You two seem very happy together,” Benny said, glancing over at Dean. Dean nodded, smiled softly.

“We are,” Dean said. And then, he took a step forwards, a step that was probably dangerous, at least slightly. “And we’re very open at this point, with each other, y’know, with what we want,” Dean told Benny, giving him a suggestive look. Understanding seemed to flicker in Benny’s eyes.

“There a reason you’ve been comin’ to see me so often?” Benny asked calmly, his voice just a little lower, spoken in a tone that made Dean shiver. Dean swallowed thickly, looked over at Benny. They made eye contact for what felt like months to Dean but was actually a few seconds.

“Cas is just,” Dean began, looking away. He wasn’t so sure he could keep looking at Benny with Benny looking at him like that. “He immediately liked you when we met. It was coincidence that you and I… had history,” Dean went on, his thumb dragging up and down over the cool glass of his beer bottle. Dean bit his lip, pausing. “I figured I could catch up with you. Come talk to you and see what you were up to,” Dean supposed, glancing back over at Benny. 

“Cas is in this picture? Or is it just you and me?” Benny questioned. Dean let out a breath.

“Cas would-” He paused. “ _I_ would like Cas to be in the picture, and so does Cas,” Dean told Benny. “I would never cheat on Cas,” Dean added on, looking back at Benny who just nodded.

“So, you’re saying that you’d wanna get back together with me, but keep Cas in the picture too?” Benny supposed. 

“Uh, not exactly,” Dean replied. “It’s less the relationship ordeal.”

“Sex with no strings attached?” Benny asked calmly. Dean glanced at Benny out of the corner of his eye.

“Well, the ‘no strings attached’ thing, Cas and I figured we’d talk to you about. If you were willing. Are willing,” Dean corrected. Benny paused, raised an eyebrow.

“A threesome?”

“Well, uh, that was what I was getting at,” Dean managed, thankfully without choking on his spit. Benny seemed extremely calm, to Dean’s minor surprise. Benny was always a calm and collected guy, but Dean figured that even calm and collected guys might get a little worked up if asked about a threesome.

“How does Cas feel about this?” Benny questioned.

“Well, I’ve talked to him about it and he’s… enthusiastic,” Dean finally finished. Benny nodded once more. Dean took a deep breath and sighed. “I figured that, as long as you’re willing, we could all go out and talk about it a little. Discuss things. Only if you want to,” Dean added on. Benny shook his head and huffed a breath of laughter.

“Y’know, I said I knew I hadn’t seen the last of you, but I didn’t think that I was gonna end up in a bar with you trying to reel me into having a threesome with your boyfriend,” Benny said, grinning. Dean blushed, opened his mouth and closed it. “I mean, honestly,” Benny sighed, shaking his head once more. “I’m up for it.”

“Really?” Dean questioned almost incredulously. Benny just grinned and shrugged.

“Why not?”

\---

Less than a week later, Dean, Benny, and Cas found themselves in Benny’s diner that had been closed just for the occasion. No one else was there, they all figured that going to a public restaurant to discuss the dynamics of a threesome wasn’t too good of an idea.

They had all been fairly relaxed, the air wasn’t too tense or anything, something that everyone was thankful for. They didn’t even get straight to things, they just talked for a bit about different things, seemingly got comfortable enough with each other Cas finally piped up after a short silence.

“So, Benny,” Cas began from where he was sitting in a booth with Dean next to him, Benny on the other side of both of them. “Dean told me that you talked about… things,” Cas trailed off with a coy smile as he leaned his forearms on the table. Benny quirked a smile back at him.

“Well, he told me a few things, didn’t get too specific,” Benny told Cas who nodded.

“I just wanted to make sure that you were here too, y’know?” Dean said, looking over at Cas. “Just to discuss the whole,” Dean waved a hand. “Dynamic of things.”

“So, I’m assuming you two have talked a fair amount about this,” Benny ventured, leaning forwards. Dean nodded sheepishly.

“Yeah, we, uh, have discussed it ourselves,” Dean told Benny.

“But, we know it’s really important that we discuss things with you too since you’re an outside party. Dean and I are together, have been together, but with you, it’s different.” Cas smirked. “But, you have been with Dean before, so that switches things up a little,” he added on.

“That’s true,” Benny agreed with a nod.

“I mean, you two seem comfortable with each other, so I think it’s just a matter of how this plays out and what our plans for the future are,” Cas supposed.

“Well you seem even smarter than Dean put you out to be,” Benny said, grinning. Cas grinned back cheekily.

“There are a lot of things about me Dean hasn’t told you about yet,” Cas said, his tone sugary sweet. Dean almost choked because in that moment, he realized that Cas was _flirting_ with _Benny_. And, all things considered, he didn’t mind it as much as he thought he would.

“Okay,” Dean said, trying to gather not only himself but the situation. “I think we should just negotiate things. Put out our limits,” Dean proposed. 

“Well, I gotta know if this is about a relationship or just sex. Or both,” Benny said. 

“Well,” Dean sighed, glancing over at Cas. “Generally, since Cas and I are together, have been together for so long, it would be… odd to have you join in on our relationship. But, we don’t want to seem like we’re just asking for sex,” Dean explained.

“But, unless we’re making this a one time thing, some sort of relationship has to be considered,” Cas pointed out.

“That’s true,” Dean said reluctantly.

“Personally, I say we take things one step at a time,” Benny proposed. “Right now, we gotta consider some basic things, but it all comes down to the fact that you two are a couple and you have been going on a few years now. I’m not a part of your relationship, but if you’re bringin’ me in to have threesomes with you guys every other week then I admittedly have some part, right?”

“Well, exactly,” Cas said.

“It’s just a matter of how you feel. Cas and I agree that keeping the line of connection open between us and you is a good idea. We don’t necessarily think having you move in is something to consider,” Dean said, earning a snort from Benny, lightening the mood a little.

“We think it might be more of a matter of how you feel since if you get a partner for just you, individually, then we’d have to talk things over,” Cas supposed. Benny smiled and shook his head.

“Cas, I hate to break it to you but I don’t think I’ll be finding myself a partner anytime soon,” Benny informed Cas.

“So what do we keep it at now? Benny, you can be a part of our life, we can have an open line of connection with you, dating wise and sex wise and we can… reconsider if you find someone for yourself individually?” Dean proposed. Everyone seemingly looked at each other, and a collective nod was given.

“Are we on the same page?” Cas questioned after a moment. Dean nodded.

“Seems so,” Benny sighed.

“Good,” Cas sighed happily. “Now we can get to the really important part,” Cas said with a sneaky grin. “Dean tells me you’re pretty big,” Cas admitted, which gained a harsh kick from Dean’s foot under the table. “Ow!” Cas hissed as Benny threw his head back, laughed a deep laugh that made Cas smile.

“Yeah, well, Dean’s not so bad himself,” Benny told Cas as he looked over at Dean who was a rather deep shade of pink.

“Mm, I know,” Cas hummed, looking over Dean with a little smirk.

There was a tension in the air, nothing bad, just something promising, something heavy. Cas heaved a great sigh and shook his head.

“I can tell that this is gonna be a lot of fucking fun.”

\---

It was that Friday that both Dean and Cas decided to have Benny over for dinner. Everything went well, they talked and laughed, and Dean made sure to center a lot of conversation, or a fair amount at least, on Cas because he knew that Benny and Cas didn’t have as solid of a relationship as Dean and Benny had.

Benny and Cas seemed to get along really well. Cas flirted shamelessly through half the dinner, something that Dean found more amusing than anything else. Almost brought him back to the days where they hadn’t gotten together yet and Cas was just Dean’s assistant, teasing him constantly until they finally went out on a date.

After dinner, after everything seemed to have calmed down, there seemed to be some sort of pull between everyone, as though everyone was thinking the same thing, which, admittedly, they were. Obviously, Dean wanted Cas to get to know Benny better, and obviously they had to get together as a group, but it seemed now as though the prerequisites were out of the way and it was time to get down to business.

“So,” Cas sighed, clapping his hands together. “Anyone care to address the elephant in the room?” Cas questioned, a little smile tugging at his lips. Benny just raised his eyebrows and Dean glanced between Cas and Benny.

“You two have a plan?” Benny questioned, glancing between Cas and Dean.

“Well, generally we just needed to get you on our page,” Dean said, grinning almost shyly.

“You said you two talked about it?” Benny questioned. Cas grinned slyly and nodded, and Dean did so hesitantly. “Well, you must have some ideas then,” Benny drawled, still looking between Dean and Cas. 

“I have a lot of ideas,” Cas sighed, slowly rising from his seat. “But I think we should start off simple,” Cas went on as he slowly walked around the table and towards Benny. “Can I kiss you? I know it’s basic but Dean’s told me you’re an _amazing_ kisser,” Cas gushed, stepping forwards as Benny turned to face him, still sitting down. Benny looked over at Dean with a little smirk and Dean blushed.

“Well, I can’t say no to that,” Benny sighed, rising to his feet and stepping away from his seat, closer to Cas. Cas grinned wickedly, gave Benny a raised eyebrow as if in question. Benny just grinned more, something Cas took as an answer, as a yes. Cas turned just his head, looked straight over at Dean, made eye contact with him as Cas’ hands found their way to Benny’s chest, then slid over his shoulders so his arms were looped around Benny’s neck. Cas felt Benny’s hands sneak around his waist, feeling strong and broad and big. Cas felt sheer elation in him as he watched Dean’s face change, different emotions flickering over it. 

Before Cas could do anything, Benny was leaning forwards to press a chaste kiss to Cas’ cheek. Cas bit his lip, still grinning. He could feel scruff, glorious scruff that he always wished Dean had, but never did. Dean was always clean shaven for work, so Cas barely got to feel stubble. But with Benny, it was completely different. 

Cas slowly turned away to look at Benny, flicked his eyes up to meet Benny’s for only a second before Cas was pressing forwards, pressing his lips to Benny’s.

It was the utmost strangest feeling Cas had felt in a long time, but it wasn’t a feeling Cas could complain about. The fact that he was kissing another man, a man he found really fucking attractive, right in front of Dean, did amazing things to him. Lust, want, guilt, intrigue, all of it was there, mixing in the pit of his stomach.

The kiss stayed chaste for a moment as Cas got used to the feel of Benny’s lips. But then, Cas was allowing himself to deepen it, Benny giving Cas headway, letting him take things where he felt comfortable.

Even more feelings, sparks danced inside of Cas when the kiss deepened. It was barely a few seconds before Cas realized that Dean had been damn right. Benny was a good fucking kisser. He was firm, but gentle, excruciatingly slow, enough to make Cas want more.

Cas kissed back, more and more enthusiastically, more excitedly. Those feelings were starting to swell, to collect in something big. Benny made some soft noise into the kiss, and then Cas remembered he too could make noise, and Cas let out a shamelessly loud moan, his hands coming back to cup the back of Benny’s head, his neck.

Cas kissed and kissed until his lips nearly felt sore, and he pulled away, panting warm breaths against Benny’s lips.

“Well, fuck,” Cas breathed out eventually. Benny chuckled, deep and low in his chest.

“Me too, sugar,” he replied. Cas smiled at the name, glanced up to Benny’s eyes that were just slightly dark, pupils wide. Cas had almost forgotten about Dean until Dean spoke up.

“Jesus, Cas,” Dean murmured from where he was still sitting at the table. Cas grinned widely, all teeth, something that made Dean’s stomach tumble.

“Wish you’d grow stubble like this, Dean,” Cas panted, looking back over at Benny. His lips twitched back up as he brushed them with Benny’s. “I can only imagine what it feels like between my legs,” Cas mused, glancing between both Benny and Dean with a playful look dancing in his eyes. Benny groaned and Dean let out a choked off noise. “I say we go find out,” Cas said suggestively, glancing between Benny and Dean.

Dean was sure he had never booked it to the bedroom as fast as he did. But there was something about Benny and Cas, about the fact that he knew Benny, had been with Benny, had sex with Benny, then done the same with Cas, it did something strange to him. Something not entirely bad. And then there was that urge to show off, that possessiveness Dean had always had. That made an appearance, and all he could think of was that hot arousal that stirred in him when he watched Benny and Cas kiss. Just kiss for God’s sake. They’d surely be doing more. And Dean wanted that. He wanted it a lot.

“Okay, so maybe we should, um, talk about this, or, uh, discuss,” Dean began as they got to the bedroom, Cas plopping himself down on the bed, Benny closing the door, and Dean standing there probably looking like he didn’t know what he was doing because honestly, he didn’t.

Dean was thinking that maybe he should take some charge, suggest some things, get everything and everyone sorted out. He should have known, however, that with the controlling side Cas owned, it wouldn’t be happening.

“I want Benny to fuck me,” Cas stated plainly from where he was lying splayed out on the bed, propped up by the pillows. He looked utterly indifferent, but also rather turned on. Dean couldn’t help but choke at the sheer surprise of the words. Even Benny made some sound of surprise.

“As long as you two are okay with it, Benny, I want you to fuck me, Dean, I want you to watch,” Cas said calmly.

“You’re a little commander in the bedroom, aren’t you?” Benny questioned, sounding amused. Cas grinned once more.

“You should see what else I can be,” he declared, sounding far too pleased with himself.

“Wow, okay,” Dean breathed out. They hadn’t even started yet but holy shit, just having Cas and Benny in the same bedroom, planning what they were planning, Dean felt like the earth was spinning faster than usual.

“But, I say, Dean, c’mere and help me get all my clothes off. I wanna kiss you too,” Cas added on, shifting around on the bed, looking intently over at Dean. Dean blinked, then blinked, then looked over at Benny.

“I mean, that sounds good to me,” Benny shrugged. Dean took a deep breath and nodded.

“Right, okay,” he sighed, heading over to the bed, kicking his shoes and socks off before climbing up on it. Dean watched Cas wave his hand, motioning for Benny to come over, and Benny did so, slowly shuffling onto the bed as Dean and Cas moved over so that there was enough room for all of them. Cas was lying towards the edge of the bed with Dean straddling him, and Benny was at the bottom corner of the bed, just watching them. 

Once Dean was on top of Cas, Cas sighed happily at the familiarness of it, of Dean’s body. He propped himself up, wrapped his arms around Dean and dragged him down as he pressed their mouths together in a torrid kiss, no time for chasteness. 

Dean moaned softly into the kiss, shifting his body so he fit the right way with Cas. Cas was immediately arching up into him as if for show, his hands roaming and gripping onto Dean, their mouths almost frantic. They seemed to mirror the arousal the fact of a third party brought, and that was perfectly alright with both of them.

Soon enough, however, Dean pulled back, breathless, looking down at Cas who was already looking pink cheeked and ready for debauchery. Dean quirked a little grin at that as he slipped his hands up Cas’ t-shirt. Cas immediately understood, sitting up as best he could and tossing it over his head.

Immediately, once it was gone, Dean was kissing and kissing and kissing all over Cas’ body, his neck, his chest, his tummy. At one point, he was kissing Cas’ tummy so furiously, Cas just had to giggle and look over at Benny.

“Enjoying yourself?” Cas questioned as Dean’s fingers hooked in Cas’ jeans. Benny looked wide eyed already as he nodded, and Cas relished in the fact. “Good,” Cas said as Dean slid down his body and Cas wriggled his hips letting Dean slip off Cas’ jeans and kick them aside with help from Cas.

“Oh,” Benny sighed softly when the jeans were off. Dean glanced at where Benny’s gaze was, and so did Cas.

“Oh, I hope you don’t mind,” Cas said, nodding down to the baby blue, lace and satin panties that held his half hard cock. “I like wearing them, Dean likes seeing me wear them. It’s kind of a normal thing at this point, but it’s not for everybody,” Cas went on, flopping back against the pillows. Benny shook his head.

“Your little cock looks mighty cute in those, honey,” Benny told Cas. Cas’ cock visibly twitched at the words coming from Benny’s mouth, and Benny smiled.

“Doesn’t it?” Dean joined in, spreading Cas’ legs a little, running a finger along the line of the panties.

“You should see all the pairs Dean’s bought me,” Cas breathed out shakily as Dean ran his hand over the bulge in Cas’ panties. Dean’s lips brushed the spot just above Cas’ knee and Cas shivered as they slowly began to move upwards.

“Bet you look real pretty in all of them,” Benny mused, watching Dean’s mouth grow closer and closer to Cas’ cock.

“Dean tells me I do,” Cas moaned when Dean started mouthing over Cas’ cock through the thin fabric of the panties. Cas’ hand came down, fingers threading through Dean’s hair, tugging just the slightest. There was warmth and dampness over just the right spot, but infuriatingly, it wasn’t enough. Cas could feel his cock hardening, starting to strain against the panties until he was whining, his hips squirming.

Dean finally pulled away, kissed Cas’ stomach sloppily before sitting back. He paused for a second before looking over at Benny. 

“Do you…?” Dean trailed off in question. Benny quirked a grin, moving closer to Dean on the bed.

“Yeah, but one thing first,” Benny said before cupping Dean’s chin and pressing their lips together. Dean made a sound of shock into the kiss, but didn’t pull away, just let his eyes flutter shut.

It felt so strange to kiss Benny again, after all those years. Somehow, however, it still felt nice, still felt somewhat the same. It was almost dulled though, not as intense. It wasn’t like kissing Cas, but it had a sort of thrill that made up for it. The thrill of knowing Cas was watching, the thrill of feeling as though it was wrong, even though it felt so right.

The kiss could only be deepened for a few moments, starting to grow messy and sloppy when Cas piped up with a loud whine. Dean pulled away, looked over at Cas who looked like he was begging with his eyes. Dean couldn’t help but crack a little smile.

“Alright, sweetheart, just hold on,” Dean said as calmly as he could. Dean slid off the bed, immediately shedding his clothes, layer after layer before he was naked, and the only one still dressed was Benny. Though, that didn’t take long to change.

As Dean fumbled for lube in their bedside drawer, Benny did the same as Dean and shed all of his clothes until he was naked. Cas took absolutely no time letting his eyes roam Benny’s body. 

Benny was built different from Dean, broader shoulders, broader overall. There was a lot more hair pretty much everywhere, but Cas didn’t mind one bit. Benny wasn’t overweight, but he was muscular, and, in that sense, bigger than Dean. And then Cas remembered what Dean had said and his eyes trailed downwards…

“Holy shit,” Cas breathed out when his eyes were met with the sight of Benny’s cock that wasn’t even fully hard but was still bigger than Dean’s. When Benny realized where Cas’ attention was directed, he laughed, climbing back up on the bed.

“It’s not that big,” Benny assured Cas who gaped at him. Sure, Cas had seen some pretty big dicks in porn, but in real life, he had never seen someone as big as Benny.

“He just likes to say that,” Dean grumbled as he climbed back up on the bed, lube in hand. Cas huffed a breath of laughter and shook his head. “Here,” Dean went on, straddling Cas. “We need to get these off too,” Dean said as he hooked his fingers in Cas’ panties and tugged them down, letting Cas’ cock spring free, slapping his stomach and leaving a shiny spot of precome behind.

Dean tossed the panties aside and Cas sighed happily at the cool air against his cock. He looked between both Dean and Benny, and they both seemed to be eyeing him as though he were a particularly delicious meal. The prospect of it made satisfaction flow through Cas. It was good enough when Dean looked over him like that, when Dean paid attention to him, but to have Benny added into the mix was amazing.

“So,” Cas began with a sigh. “Dean, you know how I like to be fucked, right?” Cas questioned. Dean’s cheeks that were already pink darkened as he licked his lips.

“I mean, in general, I guess. Some nights are different but I have a general idea,” Dean said cautiously. Cas quirked a smile.

“Why don’t you lead Benny through it then? Tell him just how I like to get fucked,” Cas said smoothly, glancing over at Benny, making eye contact. Dean audibly swallowed.

“You’d, would you like that?”

“I’d love it,” Cas told Dean. “If you slip up though, say something wrong or anything I’ll chime in. You don’t know _everything_ after all,” Cas said, beginning to sit up. “So, now, Benny. How do you want me?”

Benny opened his mouth and closed it.

“Don’t be shy. Dean and I have tried lots of different positions, and I’m pretty flexible so it’s really a matter of how you want me,” Cas told Benny who seemed to think for a moment.

“You’d be okay on all fours?” Benny questioned. Cas grinned, wide and slow.

“I’d be _elated_ on all fours,” Cas said, happily rolling over onto his stomach.

There was a pause in the air where it seemed like everyone was sort of digesting the lead up of events, of what was about to happen. Cas just laid there, glancing between Dean and Benny. Benny stared at Dean. Dean just stared at Cas, let his eyes roam his body. Dean finally took a breath and sighed.

“This is so weird,” he murmured before crawling over Cas, getting onto the other side of the bed where he would have a better view.

“In a good way, I hope?” Benny supposed as Dean handed him the lube. Dean nodded.

“Yeah, I would definitely say. This is good.” Dean thought over what was about to happen, exactly what was about to happen, and he could practically feel his mind bending to accept the fact. But not in a bad way. “Weird in a very good way,” Dean went on, sitting to the side as Benny shifted so he was more behind Cas. Cas immediately propped himself up on all fours, spread his legs and let his forearms rest on the bed, his head lying on top of them. Benny took in the sight of him, all tan, smooth skin, and let out a breath.

“Hope you like what you see,” Cas piped up, smiling softly, his head tilted so that he could look at Dean and Dean could see him. Benny shook his head.

“You’re definitely a sight, sweetheart,” Benny mused, bringing a hand up to smooth over Cas’ thigh. Cas let out a shaky exhale at the touch. Benny’s hands were rough, more calloused than Dean’s, but still, they were gentle. Benny ran his hands up and down Cas’ thighs a few times, and Cas could already feel goosebumps on his skin from the touch of another man. He knew that they hadn’t even gotten that intimate yet, they had kissed, sure, but there was a lot more about to happen. Cas could only imagine his own reaction to that.

Benny’s hands then went to Cas’ hips, Cas’ back, they seemingly smoothed over every inch of skin they could get at until Cas was starting to breathe heavy just at the prospect of being touched. Silence was draped over all three men, save the sounds of breathing. Finally, Dean spoke up, breaking the silence.

“So, you’re still a tease?” Dean questioned, looking over at Benny. Benny glanced over at him with a sly smile.

“It’s not teasing, it’s foreplay,” Benny argued nonchalantly. Cas huffed an impatient breath of air.

“Maybe you could speed up the foreplay then?” Cas questioned. Dean smirked.

“Cas gets impatient if he’s really in the mood to get fucked. He can be a little bratty, just needs to be put back in his place,” Dean explained, earning a glare from Cas.

“That true?” Benny questioned, pulling his hands away from Cas, sitting back, reaching for the lube.

“It’s true that Dean likes putting me in my place,” Cas said, raising an eyebrow at Dean. Dean raised one right back.

“It’s true Cas loves to be spanked,” Dean shot back. Cas grinned at that.

“Sometimes Dean whips me if I’m really bad,” Cas told Benny who huffed a breath.

“Kinky,” he murmured, clicking open the cap of the lube. That gained a laugh from Cas, and a smile from Dean.

“Dean and I aren’t as vanilla as most,” Cas informed Benny.

“Well, I kinda figured that out to an extent. Most vanilla couples aren’t willing to have threesomes,” Benny said, glancing over at Dean who quirked a little grin. Cas snorted at that.

“Yeah, I suppose so,” he hummed.

“Okay, it’s gonna be a little cold sweetheart,” Benny warned as he drizzled some lube on a few fingers. Cas simply hummed in response, waiting just a moment before there was a cool, slick finger at his rim. He took in a breath, let it out and relaxed. Soon enough, that single finger was pushing past Cas’ rim, sliding slowly and smoothly into him, one knuckle at a time until it was settled fully into Cas. Cas had to let out a soft moan. 

“That good, sugar?” Benny questioned, twirling his finger around just a bit, not thrusting it yet.

“God, yes,” Cas sighed. “You’ve got such thick fingers,” he mused.

“I hope that’s a good thing,” Benny chuckled, slowly pulling his finger out, sliding it in.

“Trust me, it is,” Cas replied, letting his eyes close. It felt odd to have someone else’s fingers inside of him. The way Benny moved even just that single finger, it was different from the way Dean did. Not necessarily in a bad way, but just in a different way.

Meanwhile, for Dean, he was still trying to accept the facts in front of him. To see Cas lying on the bed with his ass in the air and someone else’s fingers inside of him, it definitely did something to Dean. Dean wasn’t even thinking to touch himself, he just watched both Cas and Benny, kept a careful eye on Cas’ face, his expression. And, soon enough, Cas was asking for a second finger and a second finger was slipped in. Dean listened to a soft moan fall from Cas’ lips, and Dean could only imagine how Cas was feeling about everything. And Benny, for that matter. 

“So, is it fun to watch me get fingered or are you just jealous?” Cas questioned, his eyes flicking open, looking over at Dean while a little smirk danced lightly on his lips. 

“I think both,” Dean sighed shakily after a moment. Cas grinned only more at that.

“You think you’ll come just from watching him slide his cock into me?” Cas questioned, voice playful. Dean couldn’t hold back a groan at that.

“You got a mouth on you, don’t you?” Benny huffed from behind Cas. Cas grinned wickedly.

“Dean doesn’t hesitate to gag me if I back talk too much. But right now, I have a feeling he wants to hear everything I have to say,” Cas explained.

“I think I do too,” Benny admitted, curling his fingers in just the right way, making Cas groan. “You sound like you got some pretty moans in you too,” Benny added on.

“I can be as loud as you want me to,” Cas told Benny, his hips rocking back into Benny’s fingers. “Mm, add a third one,” Cas sighed out only a moment later. Benny didn’t hesitate, just eased in a third finger that offered a pleasing stretch to Cas. 

Cas relaxed even more into it, rocked his hips back into it. Benny’s fingers were thick, but somehow they were nimble too. They weren’t fumbling and unsure, they were smooth and steady and stretched Cas in the perfect way. Cas loved Dean’s fingers, of course he did, he would never forget how it felt for Dean to finger him open, slow and sweet or rough and wanting. But Benny’s fingers were new and there was an exhilaration there because of that. There was something there that turned the usual ache or slight burn into something like a throbbing, a want, a need for more.

Cas relished in that feeling, the physical and emotional feelings that were swirling through him. He was eager, definitely, but he had seen how big Benny was, he knew he needed to be stretched, probably a little more than usual. So he calmed himself down, waited what felt like forever before speaking up.

“Okay, I’m good,” Cas sighed, blinking his eyes back open. Benny’s fingers stilled inside of Cas.

“You sure, honey? I don’t wanna hurt you or anything,” Benny said carefully. Cas shook his head.

“I can take it,” Cas assured Benny who simply sighed and let his fingers slip out of Cas. Cas bit his lip, held back a dissatisfied noise at the loss.

Dean watched from the side as Benny picked up the lube, drizzled some over his cock and stroked himself a few times, probably just for show, but Dean wasn’t complaining at all. Cas’ eyes flickered over to Dean.

“Watch. Watch every movement. I wanna see the look on your face when you watch another man fuck me,” Cas said, slow and sure and steady with that same smirk on his lips. Dean swallowed thickly, glanced between Benny and Cas.

“Yeah, okay,” Dean managed to breathe out.

“You ready, sweetheart?” Benny questioned, pressing his cock to Cas’ rim. Cas couldn’t help but gasp a little. Benny felt even bigger than he looked.

“Yes,” Cas managed, fingers clenching and unclenching.

“I’ll go slow,” Benny assured Cas, letting him nod before guiding his cock into Cas, sinking in slowly, inch by inch.

With every inch Benny slid into Cas, Cas moaned even louder. Benny was better than Cas could have imagined, better than Cas could have thought. The mixture of feelings from the fact it wasn’t Dean, and the fact that Benny’s cock was one of the biggest one’s Cas had had in him, it all flowed through him in a wonderfully hot form of chaos.

“Jesus fuck, Benny,” Cas choked out once Benny had his hips flush to Cas’ ass. “God, you feel so fucking good,” Cas then sighed out, glancing over at Dean. Dean, to Cas’ great pleasure, looked like he had just witnessed something miraculous. In Cas’ opinion, he had.

“What’s it like?” Cas questioned, his voice breathy. Dean opened his mouth, but no words came out. Cas grinned, opened his own mouth to talk some more. “We haven’t even gotten started. Benny’s gonna fuck me nice and hard. I’m probably gonna come on his cock,” Cas breathed out. 

“God,” Dean choked out. 

“You do have a filthy mouth, don’t you?” Benny mused as he began circling his hips, getting used to the tightness, the heat he was now sheathed in. 

“You have no clue,” Cas said smugly. 

“You tell me when you want me to start,” Benny said kindly. Cas took a few deep breaths, clenched and unclenched around Benny. 

“Now. I’m good,” Cas added on, closing his eyes for a moment. He heard Benny take a breath behind him before Benny’s hips pulled back just so, then thrust back in. 

Benny took mercy on Cas, started off slow, started off with solid thrusts that weren’t too harsh. Cas got used to Benny, to the thickness of his cock, and somehow, Benny and Cas seemed to be more in tune that initially thought. Soon, Benny was thrusting in harder, Cas was rocking back against him, and everything between them seemed to grow, to heat up. Dean was pretty sure he was going to come without even touching his cock. 

Cas looked over at Dean, shifted his arms so he could grip at the sheets, have more leverage to fuck back into Benny. Cas eyed Dean, looked over where he sat back on his heels with his lips parted in what must have been awe, his dick hard and curving up towards his stomach.

“C’mon, Dean,” Cas breathed out. “You’re supposed to be talking too, leading Benny through it. I can’t do all the work,” Cas said with a sly little grin.

“What do you want me to say?” Dean croaked, because he couldn’t possibly just... lead Benny through things. 

“Whatever comes to mind,” Cas replied. Dean took a breath and looked over Benny and Cas, the way Benny’s hips were moving into Cas and the way Cas’ were moving into Benny’s. There were about a million things running through Dean’s mind on certain things Cas liked, certain things Dean could tell Benny about. Dean finally swallowed and spoke.

“Cas liked to be manhandled a lot, and he likes when you push him down, really make him submit. He likes to be tied down so he can struggle, but if he’s not being tied down he wants to get fucked into the mattress, pressed into it,” Dean explained, trying to keep the hoarseness out of his voice. Dean watched Benny’s hand, his right one, come up to Cas’ hip, then his lower back, slide down and down and down until it was pressed firmly between Cas’ shoulder blades.

“Fuck, you’re strong,” Cas managed, muffled into the sheets.

“Too much?” Benny questioned, going to lighten up. 

“No, no. Dean’s right,” Cas sighed.

“If you say so,” Benny replied, splaying out his fingers, letting his palm flatten on Cas’ back.

“How rough do you want it, Cas?” Dean questioned. Cas’s tongue darted out to lick his lips as he glanced over at Dean.

“Rough enough to feel something.” Cas’s lips twitched into a grin. “Benny’s barely trying.”

There was a second there, a second of silent communication. A second where Cas seemingly dared Dean, dared him to do something. Dean raised an eyebrow and Cas just gave some sort of little nod. Dean just prayed they were on the right page…

“Spank him. Just once.”

Cas’ eyes flashed and bingo. Dean knew then and there that Cas and him had been on the right page. Benny gave Dean a raised eyebrow, glanced over at him as if in question.

“You alright with that, Cas?” Dean questioned, just to be careful. He knew this was new, he knew Cas and Benny hadn’t really done anything like this before, and the last thing Dean wanted to do was make Cas do something he didn’t want.

“Yes,” Cas breathed out, his eyes hopeful as he looked over at Dean. Dean only glanced at him before nodding over at Benny. And then, only a second later, Benny’s hand, the one that wasn’t resting between Cas’ shoulder blades, pulled back and came forwards with just the right amount of glorious force, landing on Cas’ ass. It wasn’t as hard as Dean had spanked Cas, but it wasn’t weak, Cas figured half of that being the fact that Benny’s hands were a lot bigger, a lot thicker and stronger. Cas couldn’t help but let out a yelp that echoed through the bedroom, dissolving into a soft, shaky groan.

“That okay?” Benny questioned.

“Christ yes,” Cas moaned, his back arching just a little more. “Again, please,” Cas added on. 

Benny glanced over at Dean, and Dean held back a grin.

“Make him beg.”

“Oh, fuck you, Dean,” Cas groaned, managing a glare over at Dean who had to grin at that. Benny couldn’t help but let out a little laugh.

“Dean make you beg often, sweetheart?” Benny questioned, never stilling his hips, keeping them rocking into Cas at a steady pace.

“Sometimes,” Cas and Dean both answered in unison.

“Cas likes to beg sometimes, admittedly. You’ve told me that, right, Cas?” Dean questioned. Cas just shot Dean an unamused look because, alright, it was maybe a little true. “Other times, Cas begs just because I tease him for too long and he wants it so bad. Gets a little desperate,” Dean added on, sighing. Dean tilted his head, then leaned forwards, brushed some strands of rogue hair out of Cas’ face. He could already feel confidence coming back, things felt a little more easy now. “Go on,” Dean prompted, stroking a thumb over Cas’ cheekbone. Dean wished Cas was in a different position so he could kiss him. His eyes were starting to look a little wild, filled with all sorts of flickering emotions, want, need, lust, all prominent. Cas swallowed, licked his lips.

“Please,” he said, his voice soft. Dean raised an eyebrow. “Please, Benny,” Cas said.

“Tell him what you want,” Dean said quietly. Cas swallowed again.

“Spank me,” Cas said, biting his lip.

“Put it all together, baby,” Dean prompted, still stroking Cas’ face. 

“Can you please, please, spank me Benny?” Cas asked, making sure to enunciate, to speak loud enough so Dean wouldn’t ask him to repeat himself. Dean glanced up at Benny and nodded.

“Go for five times,” Dean said. Benny took a breath, pulled his hand back, and then five quick slaps were given in succession, Cas letting out soft little cries to combine with the sounds of them.

Once Benny’s hand was simply resting on Cas’ ass, soothing the reddening skin, Cas was breathing heavier than usual.

“That okay, baby?” Dean questioned, stroking a thumb over Cas’ jaw.

“Yes,” Cas whined. “God yes.”

Dean pulled back, seemingly satisfied that Cas was satisfied. He could tell by Cas’ voice, his tone, that Cas was being truthful, that Cas was enjoying everything so far.

“You okay if Benny goes a little harder?” Dean inquired. 

“Jesus, yes,” Cas breathed out, nodding as best he could. Dean looked over at Benny, gave him a nod, and Benny immediately started thrusting in harder. His thrusts went deeper at first, started out more punctuated, then began to speed up a little, get almost rougher. 

Cas relished in the sensation, the feeling of getting fucked just that much harder. Benny had been great before, but now, after the spanking, after the firm hand on his back, Cas’ cock was dripping precome, begging to be touched, and the fact that Benny was starting to fuck him harder was making him ache only more. Cas knew better, however, than to ask for a hand on his cock. Dean would never let Cas off that easy, even if Cas was dying to feel how Benny’s hand would feel wrapped around his cock. But that was for a later date.

Cas arched up into Benny’s thrusts, tried to meet them as best he could. Every thrust was deep, hard, unyielding. Cas wasn’t even really thinking about Dean since Cas had his eyes closed, he was only trying to feel Benny, to get used to the harsher thrusts. But then, he opened his eyes, looking over at Dean whose gaze had turned hungry, his cock now a deep pink.

“Touch yourself,” Cas breathed out, glancing between Dean’s eyes and his cock. Dean bit his lip, brought his right hand around, but then paused. And then, an idea hit him.

“Cas, what would you say if after Benny finished with you he got me off too?” Dean questioned, looking over at Benny even as he spoke to Cas. Benny’s hips stuttered as he looked over at Dean, raising an eyebrow.

“Oh, Jesus,” Cas managed.

“How?” Benny questioned, still thrusting into Cas.

“Handjob?” Dean suggested with a shrug.

“You’d like that?” Benny questioned. Dean quirked a grin.

“Would you like that?”

The little smirk on Benny’s face said it all.

Benny looked like he was about to speak again, open his mouth, but then, Cas let out a gasp underneath him. Benny seemingly knew exactly what that meant.

“Right there?” Benny questioned, angling his thrusts a certain way.

“Over a little, up too,” Cas began, wriggling his hips all around, trying to get Benny to hit the right spot. Finally, he did, and Cas gasped again. “There, right there, oh, Benny, right there,” Cas choked out. Benny grinned, pulled his hips back and slammed in at just the right angle.

“Fuck!” Cas nearly shouted, pitching forwards. Benny, being stronger, bigger, had a lot more force behind his thrusts, therefore, when he hit Cas’ prostate, he really fucking hit it.

Benny started up again with a newfound angle, and Cas was immediately letting Benny know how much he appreciated it. Whines and whimpers and moans and loud groans all fell from his lips and echoed through the bedroom. Cas squirmed underneath Benny, but Benny kept his hand pushing Cas to the bed and it sent a thrill through Cas. Everything started rising in this beautiful heat throbbing through every inch of Cas, that incredible pleasure causing tears to well up behind his eyes as he stopped pushing back into Benny’s thrusts, just stayed there with his ass in the air and his thighs trembling.

“Benny, Benny, please,” Cas whined as he felt that tell tale burning in his groin, spreading around his inner thighs. Before Benny could speak, Dean did.

“Pull his hair, he comes harder and quicker if you pull his hair,” Dean piped up, watching with eager eyes as Cas wriggled around underneath Benny. Benny leaned over Cas, his left hand, the one that had been holding onto his hip sliding down and taking a handful of messy, dark hair and tugging, keeping a firm grip that wasn’t too harsh but wasn’t too weak. Cas let out a high pitched, pitiful whine at that, arching up into Benny as much as he could, his hands clawing at the sheets underneath him.

“That feel good, sugar?” Benny questioned, his thrusts never faltering. 

“Yes,” Cas whimpered. “Yes, yes, yes, oh God,” he choked out. Dean was right, having his hair pulled pushed Cas closer to the edge of orgasm. Now that Benny was pulling his hair, now that Cas had been teetering on the edge for what felt like hours, it only took a few moments before Cas was coming. Benny’s name fell from his lips over and over as his cock throbbed and a wave of white hot heat and pleasure flooded every inch of him.

Cas whimpered and whined through the over sensitiveness of his orgasm as Benny’s hips kept pounding into him even more frantically. The sound of Cas’ heavy breathing mixed with Benny’s grunts that Cas could tell were coming from gritted teeth. Cas took a deep, shuddering breath.

“Inside me, please, Benny, come inside me,” Cas begged, his voice rough as he glanced over at Dean who was, at this point, relentingly touching himself, stroking his cock, something that made that dulled down pleasure in Cas twitch. Cas simply, by some miracle, held eye contact with Dean, waited until Benny was letting out a long groan, hips stuttering as he came just as hard as Cas. 

Benny let go of Cas’ hair, drew his right hand away from where he had Cas pinned down. Everything in the room was hot, everything felt sweaty, and the sounds of heavy breathing from Cas, Dean, and Benny echoed off the walls.

“Jesus Christ, you guys,” Dean finally managed, watching Benny slowly pull out of Cas and Cas simply drop down to the mattress with a huff of a breath. 

“Oh, God, that was so fucking good,” Cas breathed out, panting heavily into the pillows. “Fuck, Benny, Dean wasn’t lying when he said you were good,” Cas mumbled. Dean glanced over at Benny, who, despite looking somewhat tired, had a twinkle in his eyes and a soft smile on his lips.

“Is that what you told Cas?” Benny questioned, eyeing Dean intently. Dean swallowed thickly and nodded, feeling as if all his words had left, evaporated, his throat dry. Benny gave Dean a once over and his lips twitched into an even wider smile. “Well, as I recall, you weren’t so bad yourself, Dean.”

Dean’s name on Benny’s tongue in that context made Dean’s stomach do something funny. 

“Seems to me by what Cas has said that you still got it,” Benny went on, starting to crawl towards Dean.

“You should find out for yourself,” Dean managed. Benny gave Dean another once over, now only inches from him, sitting back on his heels just like Dean was.

“Can I?” Benny questioned, giving Dean a general glance as if asking if he could even touch him in general. Dean swallowed thickly again.

“Please,” Dean managed. He didn’t mean to sound so wrecked, but he really couldn’t help it. Before he knew it, Benny was leaning forwards, pressing his lips to Dean’s and they were kissing once more, just as they had earlier on.

Neither of them seemed to want to start out slow, so things got messy rather quickly. Neither of them minded though. Dean wasn’t exactly sure where to touch, what to do with his hands. He hadn’t been with Benny is so so long, he was wondering if maybe Benny had changed preferences, if maybe he didn’t like certain things he used to. Still, he kissed just like he used to, and that offered a certain sort of comfort for Dean.

It wasn’t long before Benny was pulling away, nosing at Dean’s cheek. Benny’s hand came out, rested on Dean’s hip.

“Alright?” Benny asked softly.

“Yeah,” Dean managed. And then slowly, Benny’s hand was creeping towards Dean’s cock, strong, rough fingers wrapping themselves around it.

Dean immediately bucked up into the touch, and a soft little ‘oh’ left his mouth. Benny’s hands were, to say the least, a lot different from Cas’. And as he started stroking Dean’s cock, base to tip, he realized the way he worked his hand was different to, but similar to what Dean remembered.

Benny had a particular way of teasing. It was sort of like blunt teasing rather than sneaky teasing. He would palm the head, flick his thumb over the tip, do downright sinful things in a nimble manner that none would suspect, then go straight back to regular, firm strokes of his hand. It was maddening, but it was wonderful.

That went on for probably a lot less longer than usual since Dean was so on edge from watching Benny and Cas’ whole show. The whole time, Benny had his lips next to Dean’s ear. He didn’t talk, but Dean just took in his breath, steady and slow and slightly ragged at first. Dean let his hips fuck up into Benny’s fist, he let himself get lost in the sensations as his mind gave him a grateful replay of the past moments that Benny and Cas had had that Dean had watched.

Dean came embarrassingly fast with a deep groan as he nuzzled into the crook of Benny’s neck and Benny stroked him through his orgam until Dean was oversensitive and whimpering. Finally, after a few moments of Benny’s hand simply stroking over Dean’s thigh, Dean moved aside and Benny backed up so that they could both look at Cas who was wide eyed and had seemingly been watching the whole thing.

“Jesus,” Cas murmured, his voice soft. He looked like the picture of debauchery, his stomach sticky with come, his hair ruffled, eyes wide and cheeks pink. Dean couldn’t help but grin. Then Benny couldn’t help but grin. So then Cas had to smile.

“We’re doing this again,” Cas stated. A collective nod was given from everyone in the room.

“Agreed.”

\---

Two months later and everything was going smoother than all three of them could have seemingly thought. It wasn’t just the sex that was good, but other aspects were coming along nicely. Benny and Dean were on an even field having discussed past history, Cas got to know Benny better, Dean and Cas’ relationship wasn’t suffering since they still made sure to save time for themselves. Even with that time put aside, they’re were a lot of nights spent at Dean and Cas’ with Benny, movie nights or dinner, and there were nights Dean and Cas spent at the diner with Benny. Everything was going wonderful.

It was one night where Dean and Cas were snuggled on the couch, having some time to themselves when Cas pressed back into Dean from where he was sitting in his lap. Dean nuzzled back into Cas and Cas smiled.

“Dean?”

“Hm?”

“So, there’s something I wanted to talk to you about,” Cas began. Dean immediately knew something was up. Cas was using that careful, coy tone he used when he wanted something.

“What is it?” Dean questioned carefully.

“No, it’s nothing bad, don’t worry,” Cas reassured Dean, having recognized Dean’s tone too, that tone he had when he was nervous or anticipating something not so good. “It’s just something that I wanted to try,” Cas went on. He craned his neck, turned to Dean who raised an eyebrow. “In the bedroom,” Cas added on. Dean’s eyebrow went higher. Cas smiled a little. “With Benny.”

“Oh,” Dean said, relaxing into the couch. That wasn’t so bad. Over the past months they had had together, they had tried a lot of different things and switched some different roles. A lot of things that had been suggested had been hits, and it seemed Cas, who seemed most creative, tended to offer more hits than misses.

“I don’t know how you’ll feel about it. I was gonna bring it up sooner, but I wanted to get comfortable enough with Benny, then comfortable enough with both of you. Which, admittedly, I was when we started things out, but I mean I really wanted to make sure that we all knew each other’s limits,” Cas explained, which was good insight. When they started out, everything was comfortable, but there were still things to discover. Even after a few months, there were more things to discover, but for then, they had safewords, they had limits, they had put kinks out there. Everything was more solid.

“Okay,” Dean nodded. Cas took a little breath before speaking.

“I want to take both of you. At once.”

Dean paused and blinked, then blinked some more. Just for good measure. When Cas realized that Dean wasn’t about to reply he flopped over so that he could be chest to chest with Dean, their legs tangled on the other end of the couch.

“What do you think about that?” Cas questioned. “Obviously, we need to ask Benny, but I just wanted to talk to you about it alone before we brought it up as a whole,” Cas went on.

“You think you could take us both?” Dean questioned, looking down and raising an eyebrow at Cas. Cas just shrugged with a look of indifference.

“I’ve done it before,” Cas pointed out. But there was a flaw and a catch to that statement.

“Yeah, but only with dildos. Never two real, actual dicks, attached to people,” Dean argued. “And you know how big Benny is, right?” Dean went on. Cas rolled his eyes.

“I had no idea. It’s not like I’ve ever had his dick inside me before,” he joked dryly. Dean scoffed and nudged Cas with his leg.

“Cas, we’re both pretty big,” Dean went on.

“I can take it though. You’ll just have to stretch me out a lot,” Cas insisted, now donning a hopeful look. Dean had a lurking feeling that the puppy dog eyes were about to come into play. Dean let out a sigh.

“Cas, I don’t want to hurt you,” Dean said, running a hand up Cas’ back.

“You won’t hurt me because I know that both you and Benny will be really careful. I know that you two would never hurt me.”

Sure enough, there go the puppy dog eyes, looking straight at Dean as if Cas was boring a way to Dean’s soul saying ‘Please, Dean?’ in a soft voice. And Dean might have a problem with denying Cas things he wants…

\---

“Both of us at once?” Benny inquired, slightly incredulous, from where he sat in a booth with Dean and Cas across from him in his empty diner. Cas nodded eagerly and Dean shot Benny a look, a look much like a parent would look at the other parent at the knowledge of their kid wanting something out of arm’s reach.

“Honey, do you know how tiny you are?” Benny questioned with a raised eyebrow. Cas glared at him halfheartedly, and Benny huffed a breath of laughter. “How much you two talk this over?” Benny asked, glancing between Dean and Cas. Dean shook his head.

“Not that much. I left it with Cas that we would discuss it with you,” Dean told Benny.

“I’ve done it before, just not with a real cock. Just with dildos,” Cas said, looking over at Benny. Benny looked over at Dean who shrugged.

“He has,” Dean verified. Benny glanced back between Dean and Cas.

“And how’d that go?” Benny asked.

“Nothing went wrong,” Dean said, looking over at Cas. Cas shrugged.

“I was sore for a few days but it was definitely worth it,” he told Benny. “That’s why I think it would be worth it to do it with you guys,” Cas went on.

“Cas, baby, you know how much it would be to have both of us inside you?” Benny inquired. Cas quirked a grin.

“Yeah. That’s one of the reasons why I want it,” Cas said rather coyly. Cas caught the look Benny and Dean shared after he spoke and he sighed. “Listen, I know you two care for me, and I know you two would never hurt me. And I trust both of you and I think you’d handle me with a lot of care. If I don’t like it or one of you doesn’t like it, we take a step back, and that’s all. I just want to at least try it. And at least I have somewhat of a shred of experience with doing it with fake cock instead of real cock,” Cas finally finished off. 

There was a pause, seemingly wherein everyone though over Cas’ words. Looks were exchanged, dubious, hopeful, intrigued. Benny finally sighed.

“You know how to make a good case, sugar,” he told Cas who beamed, then immediately looked over at Dean.

“Dean?” Cas inquired, giving him a hopeful look. Dean stared back before nodding.

“Yeah, alright,” he sighed. 

Cas beamed even more at that, as if he had been assured he could win some glorious prize.

“Can we do it this Friday?” Cas questioned eagerly. Another slew of looks were given around the table.

“I guess that sounds good,” Dean said. Benny nodded.

“Suppose so.”

\---

That Friday, Dean, Benny, and of course Cas all found themselves in Dean and Cas’ bedroom, all three of them sitting on the bed, already naked. There was the slight air of arousal in the bedroom, likely from the knowledge of what was going to happen, but there were nerves there too. Everything started out leisurely though, just a few kisses here and there, soft touches before everything was brought to a halt.

“Okay,” Dean announced. “I have lube, I bought a lot because we’ll need a lot.”

“Three bottles?” Cas asked incredulously as he glanced at the bedside table.

“You can never be too safe,” Dean said, pointing a finger at Cas who just shook his head. “Also, water and fruit snacks.”

“Fruit snacks?” Cas echoed, craning his head to get a better look at the bedside table where apparently Dean had set up a camp of hidden supplies.

“This is going to be a long process, someone might get hungry,” Dean supposed.

“As in, you might get hungry?” Benny joked, looking over at Dean. Dean shot back a glare and Cas huffed an impatient breath of air.

“Dean, I’d love to hear more about your planning and your…” He flailed a hand. “Supplies. But, you’re ruining the mood,” Cas told Dean. Dean held up a finger.

“You have a point. And that’s what I wanted to say,” Dean began. “Cas, we need you nice and relaxed, right? And we don’t wanna skimp on foreplay. So,” Dean gave Benny a sidelong glance. “Benny and I figured we could really relax you.”

Cas glanced between Dean and Benny who obviously knew something Cas didn’t.

“How’re you gonna do that?” Cas questioned slowly. 

“Well, first we figured you could get nice and comfy so just lie back. Dean put some extra pillows out just for you,” Benny told Cas who glanced over at Dean dubiously before slouching down, relaxing into the pillows. “As long as you’re okay with it, sugar…” Benny began, glancing over at Dean. Dean smiled softly, reached out and grabbed two containers of lube, handing one to Benny.

“Benny and I thought we could take turns eating you out just so you’re nice and relaxed,” Dean told Cas. “You can lie on your back first since we know you’ll be kind of on all fours once we get down to things,” Dean went on. Cas couldn’t help but let out a soft moan, his cock twitching at the prospect of that. Both Benny and Dean had fantastic mouths and tongues, but they both rimmed Cas in different ways. Dean was more slow, deliberate, teasing. Benny was more sloppy and enthusiastic. Cas had no idea which way he liked better.

“We also figured,” Benny went on, slowly crouching down, glancing over at Dean who gave him a little nod. “That you could touch that pretty little cock of yours as much as you want,” Benny told Cas.

“Really?” Cas questioned softly, drawing his legs up as Benny settled between them. 

“Mhm,” Benny hummed, kissing the inside of Cas’ calf. “Like Dean and I said, we want you nice and relaxed, darlin’, we want you as content as can be,” Benny went on, kissing slowly down Cas’ thighs, his stubble dragging over soft skin, causing goosebumps to rise on Cas. “If you’re gonna take both our cocks, we want you happy and ready to take ‘em, don’t wanna force you into anything,” Benny said, his hands running down the outside of Cas’ thighs.

Cas’ heart was beating faster in his chest, his breath already sped up. Usually, Benny and Dean had him stave off touching himself, wanted him to come untouched. But the idea of being rimmed by not only Dean or Benny but both of them, then being able to touch himself the whole time, that was just heaven on earth.

“All you gotta do is sit back, okay?” Benny went on, his breath ghosting Cas’ half hard cock at that point. Cas simply nodded, and Benny got in a good position, hefted Cas’ thighs over his shoulders. He kissed the inside of each one and then he was in between Cas’ legs, his tongue hot and wet at Cas’ rim.

Cas moaned immediately, trying to spread his legs a little more, even with Benny’s firm grip on them. Cas wriggled around a little, got in the right position so that he was completely comfortable. Half of his body was telling him to tense up, but then Dean was crawling over next to him, cupping the side of his face and stroking a thumb over his jaw. Cas relaxed into the touch and Dean smiled, watching Cas melt into the pillows, into the bed.

The one thing Cas did have to admit he liked more about Benny was the scruff. Cas practically lived for the moments when Benny had an opportunity to get between Cas’ legs. That scruff was glorious, scratching and tickling the most sensitive parts of Cas, lighting something up inside of him. It made his fingers clench in the sheets, little moans fall from his lips.

Benny’s tongue was something entirely different. It was skilled, but it was messy, and Cas had to admit he couldn’t complain about that trade off. The way Benny rimmed him, ate him out like Cas was an amazing meal, it made Cas feel like he was being lavished and loved to an extent he could barely stand.

Cas laid back and took it all, tried to relax, untense all his muscles as best he could. He knew both Dean and Benny were right, he had to be relaxed if he was going to take both their cocks at once. But Cas didn’t have a doubt in mind that he could manage it.

All too soon, Benny was pulling away and Cas was letting out a pitiful whimper. Benny chuckled, patted Cas’ thigh.

“Don’t worry, sugar, I gotta give Dean a turn. And we aren’t nearly done with you,” Benny said, giving Cas a promising look.

After a moment a shuffling around, Dean was then between Cas’ legs, giving him that quintessentially Dean smile of mischief before ducking his head down and getting right to things. Cas let out a moan, arched up into Dean and threw his head back on the pillows. Dean had a totally different approach than Benny to rimming. He was so much more smoother, his skin free of even stubble. His tongue tried to prod as deep as it could and Cas made sure to let Dean know that it was appreciated, growing more vocal, a hand coming down, tangling in Dean’s hair and pushing his head towards Cas. 

Cas whimpered when he realized the filthy noises that were echoing through the bedroom. He could feel Benny’s eyes on him too and it all felt like too much. Cas was still leaning towards tensing up, but he forced himself to do the opposite, let his body loosen up until Dean was pulling away. 

Cas mewled at that, but immediately Benny was back between his legs.

“Don’t worry, sugar, I got you,” Benny assured, and then it was the same cycle over again and Cas was moaning shamelessly.

It took Cas a moment, but after a second of thought he remembered what Dean and Benny had said about touching himself. Immediately, he felt like he had won the lottery.

Cas closed his eyes, bit his lip and went to wrap a hand around his cock. He groaned at the contact of skin on skin and his legs unconsciously tightened around Benny. He stroked himself languidly since he didn’t necessarily feel the burning urge to reach orgasm, he just wanted to push himself and see where it got him, see where his limits were.

He was aware of a moaning sound that he thought was coming from him, but then realized, once he opened his eyes, it was actually Dean who was eyeing him like Cas was a hot meal and Dean had been starving for days. 

Cas immediately licked his lip, wide eyes looking over Dean. Dean’s cock was already hard, arcing up to his tummy, and Cas had the sudden urge to suck Dean off. He assessed their position, saw that with work they could probably make it work, but he knew that then wasn’t the time for it.

“Fuck, Cas, you look so fucking good,” Dean told Cas, his voice dipping low. Cas grinned a little, still biting his lip, hand still moving over his cock. Cas was about to reply when Benny pulled away, and Cas let out a whimper.

“Sorry, honey,” Benny apologized, slowly letting go of Cas’ legs, pressing a kiss to the inside of his knee. “Dean’ll take care of you now,” Benny told Cas as another shuffle happened on the bed. This time, when Dean got in between Cas’ legs, he had a bottle of lube.

“You think you’re okay to take a few fingers?” Dean questioned. Cas immediately nodded. Dean nodded back, got Cas’ thighs over his shoulders and started back where Benny had left off, his tongue licking Cas open. 

Dean did so for a few minutes before pulling away just slightly. Cas held his breath in that pause before a slippery wet finger coated in lube and spit slid into Cas with little to no resistance. Cas let out a soft noise at that and Dean poked his head up.

“That okay?” he questioned, and Cas nodded. Dean shifted again, got in a position so that his head was right between Cas’ legs, his lips right near Cas’ cock. Dean had a look in his eye, a look that took Cas a few moments to figure out. But then he realized, and he let go of his cock, eyeing Dean the whole time.

Dean smiled a little at that, at the silent communication between them, and took Cas’ cock, angled it into his mouth, and swallowed Cas down, punching a desperate moan out of Cas.

It was sweet torture to have Dean’s mouth, hot and wet on his cock, and then his finger, sliding and thrusting in and out of Cas at the same time. Cas wanted more fingers since the first one felt like nothing, but he knew Dean wouldn’t let him have another quite yet. Dean and Benny too both wanted Cas really stretched, and even Cas knew that he had to be really stretched to take them both. So he was in for a long session of fingering and rimming, which, he couldn’t really complain about.

Dean was slow, not in a teasing way but in a deliberately gentle way. He didn’t pull fancy moves with his tongue, he just slid up and down Cas’ cock, sucked him harshly then softly, combined that with his finger sliding in and out. It wasn’t much, honestly, all together, but Cas was on edge from being rimmed for so long by both of them. Cas didn’t say anything, just let out the occasional moan as he felt pleasure rocking inside of him, starting to swell. He wasn’t sure how much longer Dean planned on sucking him and fingering him at the same time, but if he did so long enough, Cas knew that he was gonna come.

Sure enough, Dean went on like that for some long moments, everything inside of Cas intensifying until he was sure that he was about to come any minute. Dean knew this too, he could tell by the way Cas was moaning and rocking into his touches. So, Dean slowly, ever so slowly, slipped in a second finger. And that did it.

It was incredibly embarrassing to Cas since it was only a second finger and it slipped in nearly as easily as the other one, but that combined pressure that pushed into him tipped him over the edge so he was moaning Dean’s name, his hips bucking under Dean’s touch.

Dean let Cas ride out his orgasm before slowly pulling off of Cas’ softening cock, yet keeping his fingers where they were.

“There we go,” Dean sighed, thrusting his fingers in a little deeper and pressing a few light kisses to Cas’ inner thighs.

“How many times are you gonna do this?” Cas panted, his eyes still closed, head back in the pillows.

“What, make you come?” Dean questioned.

“Yeah,” Cas breathed out.

“As many times as you want,” Dean told Cas who groaned. He wasn’t so sure he could handle things if Dean and Benny were gonna keep up the act they had going. “We figured we could have one of us underneath you, like in a riding position, then the other behind, so you tell us who you want where,” Dean told Cas. Cas opened his eyes and bit his lip, looked between Dean and Benny, thought of what each option would bring.

“Can you get underneath me with Benny behind me?” Cas questioned, glancing up at Dean, then glancing Benny’s way. Dean looked over at Benny who nodded.

“Sounds good to me,” Dean said, pressing another kiss to Cas’ thigh. Cas smiled, settled back happily into the pillows. “I’ll stretch you open with four fingers and then we can take things from there,” Dean went on.

“I have a bad feeling you’re gonna go excruciatingly slow,” Cas murmured. Dean laughed a little at that.

“Honey, we all gotta go slow,” Benny said, smiling softly from where he sat watching Dean and Cas. “You really are small.”

“I’m not _small_ ,” Cas huffed, though, alright, he kind of was. At least compared to Dean and Benny. Especially Benny.

“You believe what you want, honey,” Benny said, crawling over to Cas, brushing a kiss over his lips. “Doesn’t matter though ‘cause we’re gonna go nice and slow and we’re gonna make you feel real real good, alright?” Benny told Cas softly. Cas looked up at him and nodded. Benny smiled down at him, pressed another kiss to his lips, this time with more intent. Cas relaxed into it, sighed and let his lips part.

Cas had learned over time that Benny was a fucking amazing kisser, so Cas had no problems kissing him at any times. And then was no exception. 

It was sloppy, off center, since Cas was in a strange position and Dean was there too and Benny was to Cas’ side. Cas didn’t mind though, just kissed Benny all slow and languid, one hand cupping Benny’s face, the other hand curled in Dean’s hair as Dean kissed and sucked and bit up and down the inside of Cas’ thighs.

Cas wasn’t hard yet, was still in his refractory period, but he didn’t mind. It still felt nice to have Dean lavishing his attention to every spot in between Cas’ thighs, and Benny kissing Cas with a steady sort of enthusiasm. Cas finally pulled away from the kiss when he wanted to take a break to breathe and then Benny was on Cas’ neck, licking and sucking bruises. At that same time, Dean pulled away from Cas’ thighs to speak.

“Can you take a third?” Dean questioned. Cas only glanced at Dean and gave him a nod. Dean then pulled out his fingers and Cas furrowed his brows.

“Where exactly are you going with those?” Cas questioned. Benny snorted into Cas’ neck at the question, and Dean grinned.

“More lube,” Dean told Cas. “I told you we need a lot. I’m gonna use as much as I can,” Dean went on.

“Don’t use too much,” Cas warned as three fingers slowly sank into Cas.

“I won’t, don’t worry,” Dean replied, soothing his free hand over the outside of Cas’ thigh.

“Don’t gotta worry ‘bout a thing, sweetheart,” Benny assured softly into the skin of Cas’ neck. “Just gotta let us take care of you,” he added on.

“Mm, you guys are doing a pretty good job so far,” Cas said with a lazy smile. Cas felt Benny grin into his neck. 

“That’s good to hear,” Benny murmured, kissing Cas’ neck softly. Cas sighed happily, hummed softly in response as he focused more on Dean’s fingers than Benny’s kisses.

With the way Dean had gone so slow and gotten Cas ready with the rimming, those three fingers inside of Cas were sliding in and out a lot easier than usual. There was a slight stretch, but everything was so slick that there wasn’t really that slight burn, not yet at least. Cas suspected that once they got to maybe a fourth finger or a few fingers added onto a cock that that burn would be there. Cas wasn’t worried though, nor was he scared. He was more excited than anything else.

No one really spoke for awhile. Benny kissed over Cas’ neck, Dean kissed Cas’ thighs and those three fingers thrust and slid in and out of Cas over and over until Cas’ cock was starting to fill out again. Dean happened to notice and he smiled a little.

“How do the three fingers feel?” Dean questioned. 

“Good,” Cas hummed happily.

“How do you feel about a fourth?” Dean asked. Cas poked his head up a little, just so he could see Dean. “I know I usually don’t stretch you with four,” Dean went on. “But I think even a little extra is good.”

“I can take a fourth,” Cas told Dean truthfully. 

“You’re sure?” Dean questioned. Cas nodded and Dean took a breath, pulling his fingers out of Cas very slowly. Cas let out a soft noise at the emptiness, but didn’t complain. He simply waited until Dean had coated all his fingers, save his thumb, in a generous amount of lube. “Okay?” Dean questioned, positioning them at Cas’ entrance. Cas nodded. Cas had some sort of feeling that maybe four fingers should feel daunting but they really didn’t. It had felt more daunting when Cas had Benny fuck him for the first time.

Those fingers slid in with some resistance. Cas didn’t tense, just relaxed into it, let those fingers fill him up. His cock twitched when they were fully inside him. Dean caught the motion and grinned.

“Good?” he questioned. Cas nodded and sighed shakily. Cas expected Dean to go back to kissing around his thighs, but then all of the sudden his mouth was moving heading towards Cas’ nearly hard cock. Cas took a sharper intake of air, poking his head back up just in time to see Dean slide back on his cock once again.

“Oh, God, Dean,” Cas groaned once Dean had most of Cas’ cock in his mouth. “You think I’m gonna fucking last if you keep this up?” Cas managed. Benny laughed at that, nipping at Cas’ ear.

“You’ll do just fine, sweetheart,” Benny reassured Cas who let out a shaky moan. “You know how pretty you’ll look sitting on both our cocks?” Benny questioned. Cas slid his hand around the back of Benny’s neck and let out a soft moan. “Cute little thing like you full of cock,” Benny went on. Cas moaned louder at that, went to chase after Benny’s lips with his own. “You already look so pretty when you get fucked, honey,” Benny murmured against Cas’ lips. Cas grinned against Benny’s lips, wide and unfaltering.

“I know,” Cas muttered, nipping at Benny’s lower lip. Benny paused, then chuckled before going in for another kiss, deeper this time. Cas relished in it, put more passion into it as he tried to make sense of all the feelings around him. Benny was kissing him furiously, Dean was fingering him, and Dean’s mouth was hot and wet on Cas’ cock. Cas was pretty sure that, even though, at previous past points, he had staved off orgasm for long periods of time, he wasn’t going to last long. And he was right.

Cas came only a few minutes later, groaning at first, then whimpering into Benny’s mouth as the oversensitivity of a second orgasm washed over him. His hips stuttered and twitched until Dean was pulling off of his cock and Benny was pulling away to let Cas breathe, take a second to collect himself.

“Jesus,” Cas breathed out, his head flopping back. He took in a deep breath and let it out.

“How do the fingers feel? You feel stretched enough?” Dean questioned. Cas nodded, still trying to catch his breath.

“I can take at least one cock now. I don’t think there’ll be a problem with that,” Cas told Dean. 

“How do you guys want to do this?” Dean questioned, glancing between Cas and Benny. “If I’m under Cas, and you’re behind him,” Dean began, glancing over at Benny. “Where should Cas go first?”

“Your cock,” Cas sighed out, letting his head pop up so he could look at Dean. “If I sit on your cock like I’m gonna ride you, then I arch my back the right way, I think it’ll be easier for Benny to slide his cock in. He’s gonna have to finger me first, obviously, but then even that’ll be easier,” Cas went on. Benny nodded, then looked over at Dean who nodded too.

“Pretty sound logic,” Dean said. “Okay, I’m gonna take these out now,” Dean warned Cas, obviously referencing his fingers. Cas reluctantly nodded, let Dean’s fingers slide out of him being replaced with only an empty feeling.

“Okay,” Cas groaned, shifting, awkwardly sitting up then immediately heading for the bedside table. “I just need water, Dean you can go lie down,” Cas stated, grabbing a water and opening it up.

“Bossy,” Dean muttered as he crawled to the middle of the bed where Cas had just been laying and flopped down. Cas took a long drink of water before setting it aside. As he did so, he eyed the fruit snacks Dean had previously mentioned. He squinted.

“Alright,” Cas announced as he crawled back over to Dean, a packet of fruit snacks in hand. Dean caught the sight of them and immediately gave Cas an incredulous look. 

“You complained about those!” Dean protested. 

“I never complained I just said we didn’t really need them. But I take it back,” Cas relented, setting them to the side. “Now here,” Cas said, grabbing a bottle of lube that had been discarded to the side, and handing it to Dean. “Put a lot on,” Cas instructed. 

Dean didn’t need to be told twice. He took the lube, popped open the cap and coated his cock in a generous amount, more than he would usually use. Cas took a deep breath and straddled Dean.

“Can I?” Cas questioned, raising an eyebrow at Dean.

“If you’re ready,” Dean replied, watching as Cas got in the right position. Cas reached around, took Dean’s cock in hand and positioned it in the right way. Slowly, with a breath, he slid down on it. Dean let out a deep groan, his eyes squeezed shut as Cas did so. Cas hummed happily once his ass was flush with Dean’s hips. He rocked back and forth, bounced up and down a little, got comfortable with it. He figured he was more stretched than usual because, again, there wasn’t that edge to it that sometimes came with taking Benny or Dean’s cock. Cas felt comfortable with it, felt stretched and open and ready. 

“Okay,” Cas sighed happily, letting himself fall forwards, grabbing the fruit snacks and tearing the pack open with his teeth. “Feels good,” Cas told Dean looking into the open pack of fruit snacks.

“You sure?” Dean questioned, running his hands up Cas’ side. Cas hummed and nodded. “You think you’re ready for a few fingers?” Dean questioned. Cas nodded, reaching in and grabbing one of the fruit snacks, popping it into his mouth.

“Benny, if you wanna start up using your fingers, I think I’m ready,” Cas called over his shoulder as he craned his neck so he could catch a glimpse of Benny.

“Can I sneak a fruit snack first?” Benny questioned, quirking a grin. Cas grinned back, held out the bag and let Benny take one of the little strawberry ones.

“You guys were all against those and now,” Dean huffed.

“Hush,” Cas said, pulling out a grape one and offering it to Dean. Dean gave Cas a look but accepted the fruit snack. There was only a moment’s pause before Cas heard another lube cap click open.

“Alright, honey, you ready?” Benny questioned from behind Cas. A flicker of something, maybe excitement, flared through Cas as he replied.

“Yeah.”

In a second, Cas felt one slick finger tease at his rim that was already stretched around Dean’s cock. Cas sucked in a breath as he felt that finger slowly slip in alongside Dean’s cock.

“Oh,” Cas breathed out.

“Okay?” Benny questioned.

“Yeah,” Cas replied, rocking his hips a little, getting used to the feeling of it. It was a stretch, more than any of the ones he had gotten with Dean’s fingers, but it wasn’t bad. There was almost, a barely there burn to it, but Cas was stretched enough for it to feel pleasurable. He rocked back into it a little more, listening to Dean’s breath pick up underneath him. Cas couldn’t help but grin as he took another fruit snack from the bag.

“You think you’ll come before Benny gets his cock in me?” Cas inquired, looking down at Dean with a cheeky grin. Dean tried to shoot Cas an unamused look, but it didn’t hold much venom, more indifference than anything else. “Think about it though. Your cock will be right neck to Benny’s. It’ll be like you’re grinding against each other but fucking me at the same time.”

“Oh, God, Cas.”

“Do you want another fruit snack?”

Dean wanted to glare at Cas, but he also wanted to laugh at how casual Cas was about the whole thing. He sighed.

“Yeah, fine, I’ll take another.”

Cas picked one out of the bag but Dean shook his head. 

“Are there any strawberry ones left?” Dean asked.

“Are you really gonna be picky right now?” Cas questioned with a raised eyebrow. 

“Okay, fine, give me a grape.”

“There aren’t any grape ones left,” Cas told Dean.

“Any fruit snack will do, Cas,” Dean sighed. Cas finally picked out an orange one and held it out, let Dean take it in his mouth before going back to get one for himself.

“How’s the single one feel?” Benny questioned from behind Cas. 

“It doesn’t feel like much, but there’s a little stretch,” Cas told him over his shoulder.

“You want a second one or do you wanna wait?” Benny questioned. Cas hummed, thought it over as he moved his hips around.

“Second one. I’ll let you know if it’s too much,” Cas insisted. And then, soon enough, the first finger was disappearing, and the next touch Cas felt was two thick fingers teasing at his rim. Cas let out a soft moan at the prospect of those being buried inside of him. Cas waited only a second before those two fingers were pushing in with somewhat of a resistance. It was then that Cas felt that stretch, that slight slight burn, an almost ache. But it was somewhat of an ache for more. Cas knew he couldn’t take more quite yet, he had to get used to just two fingers and a cock, but the thought of more, of three fingers, four, of having _more_ , it made something hot erupt inside of Cas.

Cas let out a louder moan as he rocked his hips back, tried to get those fingers to go deeper. He rocked back and forth for a moment, got used to the initial feeling of having two fingers inside of him.

“That okay, darlin’?” Benny questioned, one hand going down to smooth over Cas hip. Cas nodded.

“Feels good so far. There’s a little burn but it’s good. Really good,” Cas moaned as he rocked as far as he could down onto both Benny’s fingers and Dean’s cock.

“Don’t push yourself,” Dean said from where he was underneath Cas, one hand coming up to card through his hair.

“‘M not,” Cas argued with a sigh, going back to finish off the rest of the fruit snacks. “It all feels good. Can’t wait to have both of you inside me,” Cas went on, propping himself up on his hand, the other hand going down, fingers idly drawing shapes onto Dean’s chest.

“You’re gonna be sore,” Dean murmured, still carding through Cas’ hair. Cas let his eyes flutter shut as his hips kept up their leisurely pace of rocking back into Benny’s fingers and Dean’s cock.

“It’s so fucking worth it though. Two cocks at once, real cocks? Y’know how good that’ll feel?” Cas questioned, smirking, flicking his eyes back open to look at Dean. Dean was obviously trying to hold back in general, his cheeks flushed, his eyes wide. “And you.” Cas poked Dean’s chest. “Are a part of it. You get to watch me fuck myself on your cock and Benny’s cock. And you do know how big both of you are, don’t you?”

“You think you’ll like this?” Dean questioned, his voice cracking. Cas smiled, leaned down to kiss Dean softly then pull away.

“I think I will. I liked it when we did it with dildos so now that it’s two real people, people I love, it’s gonna be great,” Cas told Dean softly, his tone happy.

“You’re incredible,” Dean mused. Cas beamed at that, leaning down to kiss Dean again, this time more intensely, tongue slipping in.

Dean and Cas kissed and kissed and Benny worked on Cas, worked on sliding his fingers in then almost out to back in. Cas took in both the feelings, leaned into each offered touch, Dean or Benny’s hands coming out here and there to stroke his hair, his back, his side. Cas waited until the stretch and the ache dulled to a very pleasant ache. He knew Benny wasn’t going to push and ask about taking another finger, Cas was in charge then and there. So, Cas waited until he felt like he was in a good space, until he felt comfortable and loose enough to ask for a third.

“You sure you’re stretched enough?” Benny questioned, fingers slowing hesitantly. Cas pulled away from Dean and nodded.

“I feel stretched enough, I have for a little while but I wanted to wait long enough to be safe,” Cas told Benny.

“Alright,” Benny sighed, carefully slipping two fingers out of Cas. Cas waited patiently, only a few moments before three fingers were at the edge of his rim. Cas took in a little intake of breath at that since it felt like more, and Cas was just coming to really take it in, realize how much of a stretch it was. But, he didn’t falter, immediately relaxed into those three, thick, slick fingers slid their way into him alongside Dean’s cock. That same stretch, ache, slight burn, all of it returned in a way that wasn’t altogether bad.

“Ohhh,” Cas breathed out, clenching and unclenching around Benny’s fingers and Dean’s cock.

“How’s it feel?” Dean questioned from underneath Cas.

“Good,” Cas moaned.

“Sure?” Benny added from behind him.

“Yes,” Cas breathed out. He collected his breaths, let them out, took them in. He felt open, he felt stretched, and it was absolutely amazing. He could feel his cock starting to harden again, just from the overall stimulation. He rocked as far back into Benny’s fingers and Dean’s cock as he could settling there and just moving his hips in circles. Benny was good about it, made sure to move his fingers in the right way, stretch Cas gently but at the same time as much as possible. Cas relished in it, sweat beginning to glisten on his skin, his heart beginning to beat faster than usual.

“You’re gonna have to take a fourth one, sweetheart,” Benny chimed in from behind Cas.

“You think so?” Cas questioned, letting that vague sting dull more and more every moment.

“I think it’s best if you do, we want you as stretched as possible, don’t wanna hurt you,” Benny said.

“Add a fourth then,” Cas said breathily.

“You ready for a fourth?” Benny questioned with a raised eyebrow that Cas couldn’t see. Cas nodded. “You sure you’re not rushing yourself?” 

“I can promise you guys if anything hurts, hurts in a bad way, I’ll ask you to stop,” Cas said, speaking to both Dean and Benny. Benny took a deep breath.

“Alright,” he said simply. His fingers disappeared once more, and Cas felt even emptier than he had before. It felt somewhat strange to feel so open, even though he was sitting on Dean’s cock. Usually there was a stretch to Dean or Benny’s cock itself, but now it was like one wasn’t enough. “It might feel like a lot so tell me if it’s too much,” Benny warned as four fingers pressed themselves to Cas’ rim.

“Oh God,” Cas breathed out.

“Too much?” Benny questioned. Cas took a breath and shook his head.

“No, just, please,” Cas finally finished. And then Benny was pushing in at a teasingly slow pace stretching Cas open more and more until Cas was aware of a continuous low noise that was actually him moaning.

“Does it hurt?” Dean questioned, rubbing up and down Cas’ side, looking slightly worried. Cas shook his head.

“No, no,” Cas told him. He paused, throbbed around Dean’s cock, Benny’s four fingers. He took a minute to simply adjust since there was a burn to it, something he needed to get used to. He clenched and unclenched, just feeling everything before he started up rocking back and forth. Once he did, little moans started falling from his lips.

“Does it feel good?” Dean inquired from underneath Cas.

“Y- yeah,” Cas managed on a groan. “God, yeah,” he breathed out afterwards, shutting his eyes, letting his hips roll and rock. 

He kept that up, kept rocking into the touch of Benny, got used to that stretch, ache, burn, let it throb and pulse and transform into all different feelings, each one one that Cas relished in. It felt so good, Cas felt open, stretched. That slight pain that was there wasn’t even bad, it was good, that good kind of pain that hit Cas and made him want more. That kind that went straight to his cock and warred with that pleasure coursing through the rest of him. That pleasure from the prospect of the act, the pleasure from the stretch, the position, everything.

Cas let everything build, his cock starting to ache, starting to drip precome. Noises were starting to fall from his lips and his back was arching, trying to get in a better position, trying to get Benny’s fingers as deep as they could go. 

It went on like that for what felt like hours, Cas lost in his own head, in the feelings that were washing over him. Finally, he took a breath.

“Okay. I’m good. I’m ready,” Cas announced, trying to keep his voice from shaking. Both Dean and Benny stilled.

“Cas, baby, you’re sure?” Dean questioned.

“You sure you’re stretched enough for that?” Benny inquired. Cas nodded.

“I’m sure. I promise. Like I said, I’ll tell you guys if anything hurts to much,” Cas assured them. Benny sighed, but slowly slid all four fingers out of Cas who couldn’t help but whine at the loss. He still had Dean’s cock, but somehow he felt so _empty_. 

“Okay, just stay with me here,” Benny began as Cas heard the click of a lube cap. Cas heard a few sounds that he chalked up to be Benny slicking up his cock before there was a shuffling and changing of weight on the bed. A gentle hand came out and rested itself on Cas’ left hip. “Lean down a little for me darlin’, arch your back, yeah, that’s it,” Benny instructed as Cas did as told. “Dean, bend your legs a little more, Cas, honey, spread your legs a little too. Good, alright,” Benny sighed.

Cas couldn’t tell what Benny was doing, but from the heat of his body, he knew that he was right behind Cas. Cas’ heart was pounding, his mouth dry, his stomach tumbling with all sorts of feelings. And then, there it was, the head of Benny’s cock nudging at Cas’ rim. Cas gasped, his fingers clenching in the sheets.

“It’s okay, baby, it’s okay, just relax,” Benny soothed. Cas let out a shaky breath, then took a few more exhales. “You tell me when you’re ready, I’ll go as slow as I can,” Benny told Cas, his tone soft, kind. Cas swallowed thickly, shut his eyes. He wasn’t nervous before but nerves were starting to creep into him now that things were actually happening.

“Okay,” Cas sighed.

“Okay?” Benny repeated. Cas nodded, and then there was pressure, the head of Benny’s cock slow slipping past Cas’ rim, seemingly wider than all four of Benny’s fingers. Cas held his breath as Benny’s cock inched in even more, more and more until he was about halfway in. Then he paused. “How’s that?” Benny questioned. Cas just moaned.

“So fucking big,” Cas managed to choke out. 

“Too much?”

“No,” Cas replied carefully, assessing the feeling of Benny being in him the same time as Dean. There was that ache, a sting, a heat, all of it all at once, but altogether, it wasn’t too bad. “Gimme a second,” Cas sighed.

“You take all the time you need, sugar,” Benny soothed, running his hand over Cas’ hip.

Cas took a minute maybe, just let everything dull down a little, let most of the initial pain fade away, everything left good. Really good.

“Okay.”

“Alright?” Benny asked.

“Yeah,” Cas breathed out. Benny himself took a breath before slowly inching his cock in more and more. Cas let himself breathe steadily the whole time until all the sudden, there was nothing more to go, until Benny was completely inside of Cas. 

Cas’ mind almost exploded.

He took it in, took in every possible feeling there was to feel all at once in the most overwhelming way possible. Dean and Benny were both inside of Cas. Their cocks were both inside of Cas. And Cas was about to get fucked by both of them. At once.

All the slight pain, the ache, all of it faded with that realization, all of it faded as adrenaline took over, replaced the feeling of nerves or fear.

“Oh God,” Cas gasped.

“Are you okay?”

“Does it hurt?”

Came questions from Dean and Benny. 

“It feels so fucking good,” Cas breathed out in reply.

“Really?” Dean questioned, brushing hair back from Cas’ face.

“It doesn’t hurt?” Benny questioned. Cas shook his head.

“God, no. It feels, God, it feels amazing,” Cas followed up, letting his hips rock this way and that. Both Dean and Benny gasped at that, the feeling of their cocks rubbing against each other inside of Cas.

“Oh, Jesus, Cas,” Dean choked out when Cas started moving his hips around.

“Does that, that feels good for you guys too?” Cas questioned.

“It sure does, honey,” Benny groaned.

“Oh, fuck yes,” Dean breathed back. Cas took a breath and moved a little more, switched his position and went onto his forearms, arching his back a little, something that forced Benny deeper.

“Fuck, Benny,” Cas gasped as the feeling of fullness seemingly expanded. Cas felt Dean’s hands come up, one placing itself in the space between Cas’ shoulder blades, the other curled around his waist. Cas melted into those touches combined with Benny’s hands all over his hips. 

“You tell us who you want to move and when,” Benny piped up from behind Cas, trying not to rock his hips forwards despite how _good_ Cas felt. Cas collected himself as best he could.

“Benny, start moving,” Cas sighed. Benny took a deep breath.

“I’ll go slow, okay?” 

Cas hummed in reply. And then Benny was pulling away just slightly, offering a friction to both Dean and Cas who moaned softly in unison. Then, his hips were going forwards, all the way back so he was flush with Cas’ ass.

“How’s that?” Benny asked, soothing a hand over Cas’ hip.

“Again,” was all Cas could manage. “Oh, God, again.”

So, Benny was thrusting forwards again. And again. And again.

It was absolutely addicting, to not only Cas, but Dean and Benny. The slick slide of two cocks, the way Cas’ hips moved into it, the noises he made. Both Dean and Benny were getting not only friction, but the feeling of pressure, and Cas was getting this all too wonderful feeling of fullness, like some fulfilling moment he had been waiting for, he just never knew about.

Benny thrust into Cas, still being more careful than usual. Then, Cas accepted the thrusts, but ground down on Dean’s cock, and that action made Dean and Benny’s cocks press together incomparably.

Cas couldn’t even really talk, he got so lost in it. All he could think of was his mind bending to accept the fact that he had two dicks inside of him, that he was fucking himself on both Dean and Benny’s cock. It almost felt like something forbidden, something lewd and dirty. And that only added on a beautiful thrill to it.

Cas just let the movements of him and Dean and Benny take over. They moved rather well together, despite the somewhat awkward positioning. And after a while, they got into a rhythm, and everyone got on the same page. Everyone, Dean, Cas, and Benny, they were all lost from that point on.

Cas didn’t ask for it harder because he could work his hips harder. As he worked his hips harder, he forced Dean and Benny’s cocks together more quickly, with more significance. Therefore, Dean and Benny were seemingly rutting up against one another, yet, still pressed inside of Cas, something that made their minds bend too.

“God, Cas, you’re so fucking tight,” Dean managed to grit out at one point. Cas was usually tight to begin with, but with Benny’s cock added into the mix, Cas was unusually tight in the best way possible.

“You look so pretty like this, sugar,” Benny joined in. Cas whimpered, clenching down around Benny and Dean, punching a breathless groan out of Dean and a grunt out of Benny.

“Jesus,” Dean croaked.

“Never thought,” Cas panted, shifting his angle just slightly. “You two would feel this good,” he gasped as someone’s cock, Cas was suspecting Dean’s, brushed his prostate. He immediately shifted once more, rutting his hips down, trying to get Dean’s cock to hit the right spot. Finally, after what felt like years, he did, and he thrust down on it with another gasp. “Fuck, right there, oh Jesus,” Cas panted, starting to roll his hips down.

“Hold on, sugar,” Benny said from behind Cas, trying to still Cas’ hips. 

“Benny,” Cas whined. He had no idea what Benny was about to do but fuck if Cas was not impatient. 

Benny pulled Cas’ hips up just slightly, thrust forwards a few times until.

“Fuck,” Cas gasped, arching up as Benny’s cock went right into his prostate.

“Okay, rock back down onto Dean,” Benny instructed. Cas hesitantly did so, but was rewarded with Dean’s cock hitting his prostate. “Back up, honey,” Benny said, pulling Cas’ hips up, thrusting his own hips forward, hitting Cas’ prostate again.

“Oh, Christ, you’ve gotta be kidding me,” Cas choked out. 

“Is it too much?”

Cas answered by thrusting his hips harshly down onto Dean who wheezed at the sudden force.

“Fuck no,” Cas told both Dean and Benny, rocking his hips in the rhythm Benny had showed him. 

From then on, Cas just slowly kept on losing it.

With the way everyone was moving, every time Cas moved his hips either Dean or Benny’s cock was hitting his prostate. Cas felt like the earth was spinning around him, like there was nothing but Benny behind him and Dean below him, both their cocks inside of him.

Pleasure mounted and swelled with each moment, each movement of Cas’ hips. Things felt like they were going agonizingly slow, but the pleasure that ran through Cas with every thrust on Dean or Benny’s cock made up for it. He was aware of heat pulsing through him, throbbing and threatening to spill. Everything felt like it was cresting and cresting, and Cas wasn’t even aware of his hips moving faster or words spilling unbidden from his lips. All he knew was that glorious moment when everything snapped and he came harder than he was sure he had probably ever in his life. Little sobs and moans fell from his lips as he rode it out, clenching almost painfully around Benny and Dean.

Dean lost it at that, couldn’t take it. Everything was hot, and Dean had been on edge for the last century it felt like. So, when Cas clenched down around him, it was all over, and he was coming, moaning Cas’ name desperately as his hips bucked up into Cas.

Benny followed about a minute later, the prospect of watching Dean and Cas come almost at the same time nearly too much to handle. His hips lost control, thrust into Cas a little harder as Cas whimpered and whined from the oversensitivity.

Everyone was a mess.

Everyone was breathing heavy, Cas’ ears were ringing, Benny was probably having heart palpitations, and Dean was sure he was having an asthma attack.

And it was fucking wonderful.

“That was,” Cas panted, the first to speak. “The best sex I have ever fucking had.”

“I agree,” Dean choked out.

“Yeah, me too,” Benny breathed out.

“Okay,” Cas sighed. “Okay,” he said again, as if he was trying to take control of the room.

“You want me to pull out first?” Benny questioned. Cas nodded.

“Slow, go slow,” Cas warned.

“I will,” Benny reassured as he held onto Cas’ hips and, as slow as possible, pulled out of Cas who moaned the whole time. 

Benny sat back and soothed a hand over Cas’ hip.

“Alright?” he asked.

“Yeah,” Cas breathed. He licked his lips and shifted his hips around, giving himself a minute before slowly rising up to his knees, wincing as Dean’s softening cock slipped out of him.

Gingerly, ever so gingerly, Cas crawled off of Dean, and laid down next to him on his back, legs still spread, feeling emptier than he had probably ever had.

“You okay, sweetheart?” Benny asked, immediately going to the other side of Cas, sitting down next to him.

“Mm, yeah,” Cas replied as Dean sat up next to him.

“What do you want? Do you need anything?” Dean questioned, stroking a hand over Cas’ face.

“Probably a hot bath and a large pizza,” Cas groaned, stretching his arms over his head. Benny chuckled and Dean smiled at that.

“I think we can do that,” Benny said, leaning down and giving Cas a soft kiss. Dean immediately followed, brushing another kiss over Cas’ lips.

“How do you feel?” Dean asked. 

“Empty, a little sore,” Cas sighed, wrinkling his nose at the small amount of come that had made its way to his stomach. “But not like, in a bad way,” he rectified. “In a good way. In a way like I’d definitely want to do this again,” he said, grinning softly. Benny huffed a quiet breath of laughter.

“You’re a little trooper, aren’t you?” he said, smiling down at Cas who smiled back.

“Well, you guys deserve some credit. You were patient with me and you took good care of me,” Cas pointed out, glancing between Dean and Benny.

“Well, that’s exactly what you deserve, honey,” Benny said kindly before the act of cleaning everything up was put into place. Lube and come and sweat, all washed away, a hot bath drawn, and lots of pizza ordered for delivery.

\---

It was a few months later when Dean and Cas were driving down that same road they had gotten lost on so many months ago. Cas was looking out the car window, the drive nice and quiet as both him and Dean headed off to Benny’s diner where they decided they would have dinner together since they hadn’t seen Benny in a few weeks.

Cas sighed, and thought over everything that had been happening in the past few months. Everything had been going wonderful, honestly. The openness that Dean and Cas and Benny’s relationship offered was rather refreshing. They had their arguments, much like Dean and Cas had had when they were just Dean and Cas without Benny in the mix, but it was nothing that couldn’t be fixed. 

Cas had almost expected Benny to end up leaving, or for this threesome thing to be a month or two long thing. But it turned out to be more, and Cas found he couldn’t complain, nor did he want to. Having Benny in the mix with Dean was a lot more lovely than Cas had suspected, and not just in the realm of sex. Benny was fun to talk to, he was particularly nice, always considerate. Cas found that Benny was just as lovely to be around as Dean. Cas found that he truly did love being around Benny. 

“I’m glad we got lost on this road,” Cas spoke up, snapping Dean out of his own thoughts. Dean glanced over at Cas, furrowed his brows.

“Why?”

“Because you found Benny. And then we got to start talking to him,” Cas told Dean. Dean quirked a little smile.

“So you’re happy now, even with Benny in the picture?”

“Why wouldn’t I be?” Cas questioned, looking over at Dean. Dean shrugged.

“Dunno. Like I told you awhile ago, adding a third party changes relationship dynamics. All kinds of things can happen. Jealously or arguments or whatever,” Dean supposed.

“Things have been going really well though,” Cas pointed out. Dean nodded.

“Very true. It really has been going well,” Dean mused. 

“Are you happy?” Cas questioned. Dean smiled, glanced over at him.

“Yeah, I am. I had no idea it would lead to this but, surprisingly enough, I feel like everything worked out,” Dean sighed.

“Yeah,” Cas sighed back, smiling softly. “Everything did work out.”

**Author's Note:**

> tell me literally anything, any form of any possible interaction gives me life and i appreciate it all so so much, you don't even know <3 thank you guys so so much for reading, i hope that all of you are doing well!!! xoxo


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